Sodium borohydride → HCID 20084349, compound

HRID 1609315Notes

Reaction equation

HRID 1609315 reaction equation
[BH4-].[Na+].[C:3]([C:8]1[S:9][CH:10]=[C:11]([CH:13]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)[N:12]=1)(OCC)=[O:4]>C(O)C>[CH:13]1([C:11]2[N:12]=[C:8]([CH2:3][OH:4])[S:9][CH:10]=2)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 20084360HCID 20084360, compound

Product 1

HCID 20084349HCID 20084349, compoundYield 87.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium borohydride (6.4 g) was added in one portion to an ice cold solution composed of 25.4 g of 2-carboethoxy-4-cycloheptylthiazole and 200 ml of ethyl alcohol. The ice bath was removed after 30 min and the reaction mixture was allowed to warm to room temperature. After 16 hr the reaction mixture was diluted with 400 ml of ice water and extracted with methylene chloride. The combined extracts were washed with brine, dried (MgSO4) and concentrated in vacuo to yield 18.6 g of 4-cycloheptyl-2-thiazolemethanol as an oil.

Workup

  1. customThe ice bath was removed after 30 min
  2. additionAfter 16 hr the reaction mixture was diluted with 400 ml of ice water
  3. extractionextracted with methylene chloride
  4. washThe combined extracts were washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-67c12092e3014be5ad73f3f2e5dca266
Source dataset
uspto-grants-1995_03
Patent number
US05399702

Reaction notes

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