Ethyl Acetate → (5-Fluoro-1-benzothiophen-2-yl)methanol

HRID 1843958Notes

Reaction equation

CC(C[AlH]CC(C)C)C.[F:10][C:11]1[CH:23]=[CH:22][C:14]2[S:15][C:16]([C:18](OC)=[O:19])=[CH:17][C:13]=2[CH:12]=1.C(OCC)(=O)C>C1COCC1.CCCCCC>[F:10][C:11]1[CH:23]=[CH:22][C:14]2[S:15][C:16]([CH2:18][OH:19])=[CH:17][C:13]=2[CH:12]=1

Participants

Conditions

Temperature: -10 °C

Procedure

DIBAL-H (59.4 mL, 59.41 mmol) was added to a solution of methyl 5-fluorobenzo[b]thiophene-2-carboxylate (I-50a: 2.5 g, 11.882 mmol) in THF (75 mL) at −70° C. and the resulting reaction mass was stirred at −10° C. for 2 hours. The reaction was monitored by TLC (30% ethyl acetate in hexane). The reaction mass was quenched with methanol at −70° C. and concentrated under reduced pressure. The crude residue obtained was partitioned between water and ethyl acetate. The organic layer was dried over Na2SO4 and concentrated under reduced pressure to afford the crude product. Purification by column chromatography on silica gel (15% ethyl acetate in hexane) afforded 1.8 g of the product (83.33% yield).

Workup

customthe resulting reaction mass
customThe reaction mass was quenched with methanol at −70° C.
concentrationconcentrated under reduced pressure
customThe crude residue obtained
customwas partitioned between water and ethyl acetate
dry with materialThe organic layer was dried over Na2SO4
concentrationconcentrated under reduced pressure
customto afford the crude product
customPurification by column chromatography on silica gel (15% ethyl acetate in hexane)

Sources & evidence

ORD record: ord-5f9944555000483286c8ad2335b14e60
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08946260B2

Reaction notes

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