Acetic Acid → HCID 23204093, compound

HRID 322887Notes

Reaction equation

HRID 322887 reaction equation
[C:1]([C:4]1[CH:25]=[CH:24][C:23]([O:26][CH2:27][C:28]2[CH:32]=[CH:31][S:30][CH:29]=2)=[CH:22][C:5]=1[O:6][CH:7]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[CH3:21])[CH2:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])(=[O:3])[CH3:2].[BH4-].[Na+].C(O)(=O)C>CO>[OH:3][CH:1]([C:4]1[CH:25]=[CH:24][C:23]([O:26][CH2:27][C:28]2[CH:32]=[CH:31][S:30][CH:29]=2)=[CH:22][C:5]=1[O:6][CH:7]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[CH3:21])[CH2:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH3:2]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 4311764Sodium borohydrideHCID 10503817HCID 10503817, compound

Product 1

HCID 23204093HCID 23204093, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A stirred solution of ethyl (RS)-4-[2-acetyl-5-(3-thienylmethoxy)phenoxy]-4-(2-methylphenyl)butanoate (1 g) in methanol (50 mL) is treated, portionwise, with sodium borohydride (0.1 g), and stirred at ambient temperature for one hour. It is then treated with dilute acetic acid (50 mL; 1 N) and extracted with ethyl acetate (2×50 mL). The combined organic extracts are washed with water (2×50 mL) dried over magnesium sulphate, filtered and concentrated in vacuo. Flash chromatography on silica gel, eluting with a mixture of ethyl acetate and cyclohexane (1:5 v/v) gives ethyl (RS,RS)-4-[2-(1-hydroxyethyl)-5-(3-thienylmethoxy)phenoxy]-4-(2-methylphenyl)butanoate.

Workup

  1. extractionextracted with ethyl acetate (2×50 mL)
  2. washThe combined organic extracts are washed with water (2×50 mL)
  3. dry with materialdried over magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. washFlash chromatography on silica gel, eluting with a mixture of ethyl acetate and cyclohexane (1:5 v/v)

Sources & evidence

ORD record
ord-c1f51905a2b7469ab8f6e493d29dbf76
Source dataset
uspto-grants-2001_04
Patent number
US06211234B1

Reaction notes

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