The West Indies trail India by 270 runs in their second Test in Mumbai after getting the hosts all out for 495 in their first innings.
Earlier in the day, Sachin Tendulkar, who is competing in his 200th and final Test match, was dismissed for 74 in what could be his final innings at the crease.
After tea, Rohit Sharma managed to push on for the hosts by surpassing his century and ended the innings unbeaten on 111 from 127 balls, but Bhuvneshwar Kumar (4) eventually fell, as did Pragyan Ojha for a duck.
Mohammed Shami (11) was the final batsman to be dismissed before the West Indies took to the crease for a short stint on day two.
However, the visitors were unable to stay unbeaten until stumps as Kieran Powell and Tino Best were both dismissed on nine runs, while Darren Bravo was taken out for 11.
Chris Gayle (6) remains unbeaten at the crease as the visitors closed the day on 43-3 in their second innings.
