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

HRID 1648504Notes

Reaction equation

HRID 1648504 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.B.C1COCC1>[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

4

Reactant 1

HCID 867445382,3-Bis(mercaptoisobutryl) propionic acid

Product 1

HCID 867445372,3-Bis(mercaptoisobutryl)propanol

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 2723981Borane;tetrahydrofuranSolvent

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-fb40702f5097419ba1326776339c536e
Source dataset
uspto-grants-1995_07
Patent number
US05436352

Reaction notes

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