Water → 11-Mercaptoundecanol

HRID 1279132Notes

Reaction equation

HRID 1279132 reaction equation
[SH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12](O)=[O:13].CSC.B.O>C1COCC1>[SH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][OH:13]

Participants

5

Reactant 3

HCID 962WaterHCID 54350211-Mercaptoundecanoic AcidHCID 12423031(Dimethyl sulfide)trihydroboron

Product 1

HCID 26182411-Mercaptoundecanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

11-Mercaptoundecanoic acid (G) (1.0 g, 4.6 mmol) was dissolved in dry THF (20 mL) and borane dimethyl sulphide (3 mL, 1.1 equiv.) was slowly added under N2 atmosphere. The mixture was stirred at room temperature for 4 hr. Water was added to the solution was extracted using ethyl acetate. The organic extract was washed with 1N HCl, water and saturated sodium bicarbonate solution successively. After drying (MgSO4), the solvent was evaporated to give a clear oil. The crude oil was purified by column chromatography [eluant: hexane/ethyl acetate (8:2)]. Yield: 0.45 g (48%)

Workup

  1. extractionwas extracted
  2. extractionThe organic extract
  3. washwas washed with 1N HCl, water and saturated sodium bicarbonate solution successively
  4. dry with materialAfter drying (MgSO4)
  5. customthe solvent was evaporated
  6. customto give a clear oil
  7. customThe crude oil was purified by column chromatography [eluant: hexane/ethyl acetate (8:2)]

Sources & evidence

ORD record
ord-2f7c328821034f8d909a4f492b2d76a1
Source dataset
uspto-grants-2002_09
Patent number
US06447656B1

Reaction notes

Loading…