Sodium borohydride → 4-(6-Carbomethoxyhexyl)-5-(3-hydroxy-1-trans-octenyl)-thiazole

HRID 972241Notes

Reaction equation

HRID 972241 reaction equation
[BH4-].[Na+].[C:3]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]1[N:14]=[CH:15][S:16][C:17]=1/[CH:18]=[CH:19]/[C:20](=[O:26])[CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])([O:5][CH3:6])=[O:4]>O.C(O)(C)C>[C:3]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]1[N:14]=[CH:15][S:16][C:17]=1/[CH:18]=[CH:19]/[CH:20]([OH:26])[CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])([O:5][CH3:6])=[O:4]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 214064184-(6-Carbomethoxyhexyl)-5-(3-keto-1-trans-octenyl)-thiazole

Product 1

HCID 214064094-(6-Carbomethoxyhexyl)-5-(3-hydroxy-1-trans-octenyl)-thiazoleYield 82.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 3776IsopropanolSolvent

Procedure

The solution of 143 mg of sodium borohydride in 30 ml of water was added to the solution of 2.65 g of 4-(6-carbomethoxyhexyl)-5-(3-keto-1-trans-octenyl)-thiazole (Ia, R1 = H) in 30 ml of isopropanol. The obtained reaction mixture was stirred for 2 hours at room temperature, then poured onto 150 ml of water, and extracted with 3 × 75 ml of ethyl acetate. The ethyl acetate extract was washed with water to neutral and evaporated in vacuo. The obtained 2.5 g of evaporation residue was subjected to chromatography on a column prepared with 100 g of silicic acid, the elution was carried out with mixtures of n-heptane and ethyl acetate of gradually increasing ethyl acetate content. The desired 4-(6-carbomethoxyhexyl)-5-(3-hydroxy-1-trans-octenyl-thiazole, (Ic, R1 = H) was eluted from the column with a mixture consisting of 70 % n-heptane and 30 % ethyl acetate, affording 2.2 g of a product of chromatographic purity.

Workup

  1. customThe obtained reaction mixture
  2. extractionextracted with 3 × 75 ml of ethyl acetate
  3. extractionThe ethyl acetate extract
  4. washwas washed with water to neutral and
  5. customevaporated in vacuo
  6. customThe obtained 2.5 g of evaporation residue
  7. customprepared with 100 g of silicic acid
  8. washthe elution
  9. washThe desired 4-(6-carbomethoxyhexyl)-5-(3-hydroxy-1-trans-octenyl-thiazole, (Ic, R1 = H) was eluted from the column with a mixture

Sources & evidence

ORD record
ord-d78733f5c38d4ca4bfc1041858f0dd16
Source dataset
uspto-grants-1977_10
Patent number
US04052407

Reaction notes

Loading…