Methanol → HCID 6430883, compound

HRID 972891Notes

Reaction equation

HRID 972891 reaction equation
C([S:4][C:5]([CH3:11])([CH3:10])[CH2:6][C:7](=[O:9])[CH3:8])(=O)C.[BH4-].[Na+].[O:14]([CH3:16])[Na].[CH3:17]O>O>[C:16]([O:9][CH:7]([CH2:6][C:5]([SH:4])([CH3:10])[CH3:11])[CH3:8])(=[O:14])[CH3:17]

Participants

6

Reactant 4

HCID 887Methanol2×HCID 4311764Sodium borohydrideHCID 12997944S-(2-Methyl-4-oxopentan-2-yl) ethanethioateHCID 178418582HCID 178418582, compound

Product 1

HCID 6430883HCID 6430883, compoundYield 52.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-Acetylthio-4-methylpentan-2-one (17 g, prepared as described by R. Brown, W. E. Jones and A. R. Pinder, J. Chem. Soc. 1951, 2123), was dissolved in 25 ml of methanol. A solution of 1.945 g of NaBH4 and of 0.1 g of NaOCH3 in 25 ml of methanol was added dropwise through a dropping funnel, keeping the temperature of the reaction mixture between 10° and 25° C. by occasionally cooling with ice water. After standing overnight the reaction mixture was diluted with a same volume of water and extracted twice with n-pentane. The pentane extract was washed neutral with an aqueous solution of sodium chloride, dried over sodium sulphate and concentrated. Distillation of the residue yielded 19 g (52.5%) of 4-mercapto-4-methylpent-2-yl acetate, b.p. 37°-39° C./1 mm, nD20 1.4530.

Workup

  1. customthe temperature of the reaction mixture between 10° and 25° C.
  2. extractionextracted twice with n-pentane
  3. extractionThe pentane extract
  4. washwas washed neutral with an aqueous solution of sodium chloride
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated
  7. distillationDistillation of the residue

Sources & evidence

ORD record
ord-082424b8666d4e43a89f0aa072a4f63e
Source dataset
uspto-grants-1977_10
Patent number
US04053656

Reaction notes

Loading…