3-Mercaptopropanol → HCID 53807292, compound

HRID 231277Notes

Reaction equation

HRID 231277 reaction equation
C[O-].[Na+].[BH4-].[Na+].[SH:6][CH2:7][CH2:8][CH2:9][OH:10].CS(O[CH2:16][CH:17]([O:40][CH3:41])[CH2:18][O:19][CH2:20][CH2:21][CH:22]([CH3:39])[CH2:23][CH2:24][CH2:25][CH:26]([CH3:38])[CH2:27][CH2:28][CH2:29][CH:30]([CH3:37])[CH2:31][CH2:32][CH2:33][CH:34]([CH3:36])[CH3:35])(=O)=O>O1CCCC1.CO>[OH:10][CH2:9][CH2:8][CH2:7][S:6][CH2:16][CH:17]([O:40][CH3:41])[CH2:18][O:19][CH2:20][CH2:21][CH:22]([CH3:39])[CH2:23][CH2:24][CH2:25][CH:26]([CH3:38])[CH2:27][CH2:28][CH2:29][CH:30]([CH3:37])[CH2:31][CH2:32][CH2:33][CH:34]([CH3:35])[CH3:36]

Participants

7

Reactant 4

HCID 882113-MercaptopropanolHCID 4311764Sodium borohydrideHCID 10942334Sodium MethoxideHCID 20034844HCID 20034844, compound

Product 1

HCID 53807292HCID 53807292, compoundYield 96.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To 30 ml of teterahydrofuran are added 11.8 ml of a methanol solution of sodium methoxide (28% solution), 0.57 g of sodium borohydride and 4.14 g of 3-mercaptopropanol, to which is added dropwise a solution of 6.97 g of 2-methoxy-3(3,7,11,15-tetramethylhexadecyloxy)propyl methanesulfonate in 50 ml of tetrahydrofuran at room temperature with stirring under nitrogen streams. Thereafter, the reaction mixture is stirred at room temperature for 16 hours. The solvent is distilled off under reduced pressure and the residue is extracted with hexane. The extract layer is washed successively with water, dilute hydrochloric acid, water, an aqueous sodium bicarbonate solution and then with water. After drying, the solvent is distilled off under reduced pressure to leave 6.67 g of the captioned compound as an oily substance.

Workup

  1. stirringThereafter, the reaction mixture is stirred at room temperature for 16 hours
  2. distillationThe solvent is distilled off under reduced pressure
  3. extractionthe residue is extracted with hexane
  4. washThe extract layer is washed successively with water, dilute hydrochloric acid, water
  5. customAfter drying
  6. distillationthe solvent is distilled off under reduced pressure

Sources & evidence

ORD record
ord-4312121f65cf432d8779ef020fb166f3
Source dataset
uspto-grants-1989_07
Patent number
US04845219

Reaction notes

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