Water → HCID 54568169, compound

To the solution of 0.44 g (3.8 mmol) of Thiophen-3-ylmethanol in 5 mL anhydrous methylene chloride was added 0.58 mL (4.18 mmol) of anhydrous triethylamine and kept for stirring under nitrogen atmosphere. To the solution was then added 0.01 g (0.09 mmol) of DMAP followed by the addition of 0.29 mL (4.17 mmol) acetyl chloride dropwise and kept for stirring for 3 h under nitrogen atmosphere. The resulting mixture was poured into 50 mL of water and extracted twice from 70 mL of methylene chloride. The combined organic layer was dried over Na2SO4 and concentrated under reduced pressure to yield pale yellow liquid. The crude product was purified by silica gel column chromatography by eluting with hexane and ethyl acetate (1:1) to obtain colorless liquid. Yield: 85%. 1H NMR (400 MHz CDCl3): δ 2.08 (s, 3H), 5.11 (s, 2H), 7.09 (s, 1H), 7.31 (m, 2H). 13C NMR (100 MHz, CDCl3): δ 20.78, 61.13, 124.28, 126.15, 127.55, 136.82, 170.56.

1. stirringfor stirring for 3 h under nitrogen atmosphere
2. extractionextracted twice from 70 mL of methylene chloride
3. dry with materialThe combined organic layer was dried over Na2SO4
4. concentrationconcentrated under reduced pressure
5. customto yield pale yellow liquid
6. customThe crude product was purified by silica gel column chromatography
7. washby eluting with hexane and ethyl acetate (1:1)
8. customto obtain colorless liquid

ORD record

ord-5826be594f6c4ee5bf273e5d2ee5a12e

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08772764B2