Sodium borohydride → HCID 59252300, compound

HRID 2265916Notes

Reaction equation

HRID 2265916 reaction equation
[CH3:1][O:2][C:3](=[O:18])[CH:4]=[C:5]1[CH2:8][CH:7]([CH2:9][O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:6]1.[BH4-].[Na+]>CO.Cl[Ni]Cl>[CH3:1][O:2][C:3](=[O:18])[CH2:4][CH:5]1[CH2:6][CH:7]([CH2:9][O:10][CH2:11][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:8]1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 59252302HCID 59252302, compound

Product 1

HCID 59252300HCID 59252300, compoundYield 55.2%

Reagents, catalysts & solvents 2

HCID 24385Nickel DichlorideCatalystHCID 887MethanolSolvent

Conditions

Temperature
2.5 °C

Procedure

(3-Benzyloxymethyl-cyclobutylidene)-acetic acid methyl ester (5.4 g, 21.9 mmol) were dissolved in 80 ml methanol and cooled to 0-5° C. NiCl2 (2.53 g, 19.5 mmol) and NaBH4 (4.14 g, 109.6 mmol) were added slowly and the reaction mixture stirred for 1 hour at 0-5° C. The reaction mixture was quenched with 1N HCl and extracted two times with dichloromethane. The organic extract was washed with brine, dried with sodium sulfate, filtered and evaporated. The crude product (3.0 g, 55%) was obtained as a colourless liquid and used without any further purification for the next step. MS: m/e=249.1 (M+H+).

Workup

  1. customThe reaction mixture was quenched with 1N HCl
  2. extractionextracted two times with dichloromethane
  3. extractionThe organic extract
  4. washwas washed with brine
  5. dry with materialdried with sodium sulfate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-a5b7a30499064f9f84cc9647fe5a1dc7
Source dataset
uspto-grants-2010_12
Patent number
US07858630B2

Reaction notes

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