Water → ethyl 2-[4-(3,4-dihydro-2H-1-benzopyran-6-yl)-2,5-dimethyl thiophen-3-yl]-2-hydroxyacetate

HRID 591022Notes

Reaction equation

HRID 591022 reaction equation
[BH4-].[BH4-].[BH4-].[BH4-].[Na+].[Na+].[Na+].[Na+].[O:9]1[C:14]2[CH:15]=[CH:16][C:17]([C:19]3[C:20]([C:26](=[O:32])[C:27]([O:29][CH2:30][CH3:31])=[O:28])=[C:21]([CH3:25])[S:22][C:23]=3[CH3:24])=[CH:18][C:13]=2[CH2:12][CH2:11][CH2:10]1.O>CO>[O:9]1[C:14]2[CH:15]=[CH:16][C:17]([C:19]3[C:20]([CH:26]([OH:32])[C:27]([O:29][CH2:30][CH3:31])=[O:28])=[C:21]([CH3:25])[S:22][C:23]=3[CH3:24])=[CH:18][C:13]=2[CH2:12][CH2:11][CH2:10]1

Participants

5

Reactant 3

HCID 962WaterHCID 70855185ethyl 2-[4-(3,4-dihydro-2H-1-benzopyran-6-yl)-2,5-dimethyl thiophen-3-yl]-2-oxoacetateHCID 131720822Sodium tetraborohydride

Product 1

HCID 70855186ethyl 2-[4-(3,4-dihydro-2H-1-benzopyran-6-yl)-2,5-dimethyl thiophen-3-yl]-2-hydroxyacetate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

At 0° C., sodium tetraborohydride (10 mg, 0.26 mmol) was added to a solution of ethyl 2-[4-(3,4-dihydro-2H-1-benzopyran-6-yl)-2,5-dimethyl thiophen-3-yl]-2-oxoacetate (17d) (90 mg, 0.26 mmol) in methanol (5 mL). After 1 hour, water (5 mL) was added, the reaction mixture was concentrated in vacuo and the residue was diluted with ethyl acetate (10 mL). The organic layer was washed with water (10 mL), brine (10 mL), dried over sodium sulfate, filtered and evaporated under reduced pressure to afford the desired alcohol (17e) as a white solid without further purification (88 mg, 0.25 mmol, 98%).

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. additionthe residue was diluted with ethyl acetate (10 mL)
  3. washThe organic layer was washed with water (10 mL), brine (10 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-878035cbcb9942ea9f8aa819529e11a8
Source dataset
uspto-grants-2016_01
Patent number
US09238026B2

Reaction notes

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