2,3-Bis(mercaptoisobutryl) propionic acid → 2,3-Bis(mercaptoisobutryl)propanol

HRID 1461216Notes

Reaction equation

HRID 1461216 reaction equation
[SH:1][C:2]([CH3:17])([CH3:16])[C:3]([CH:5]([CH2:9][C:10](=[O:15])[C:11]([SH:14])([CH3:13])[CH3:12])[C:6](O)=[O:7])=[O:4]>O1CCCC1>[SH:1][C:2]([CH3:17])([CH3:16])[C:3]([CH:5]([CH2:9][C:10](=[O:15])[C:11]([SH:14])([CH3:13])[CH3:12])[CH2:6][OH:7])=[O:4]

Participants

3

Reactant 1

HCID 867445382,3-Bis(mercaptoisobutryl) propionic acid

Product 1

HCID 867445372,3-Bis(mercaptoisobutryl)propanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To an ice-cold solution of 2,3-bis(mercaptoisobutryl) propionic acid 9 (Scheme 1) (1 mmol) in 10 mL of anhydrous tetrahydrofuran, 1.5 mL of 1M BH3. THF is added over a period of 5 minutes (min.). The solution is stirred for another 10 min. and evaporated to dryness. Ten ml of water is added to the residue and the mixture is extracted with ethyl acetate. The organic layer is washed with water, dried and evaporated in vacuo to give the product 21, which is purified by flash column chromatography.

Workup

  1. customevaporated to dryness
  2. additionTen ml of water is added to the residue
  3. extractionthe mixture is extracted with ethyl acetate
  4. washThe organic layer is washed with water
  5. customdried
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-4786cb23491e40249354614047fc7a6c
Source dataset
uspto-grants-1991_12
Patent number
US05075099

Reaction notes

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