Sodium borohydride → HCID 68744317, compound

HRID 2242786Notes

Reaction equation

HRID 2242786 reaction equation
[CH:1]1([CH:7]=[C:8]2[CH2:13][CH2:12][O:11][C:9]2=[O:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[BH4-].[Na+]>[Ni](Cl)Cl.CO>[CH:1]1([CH2:7][CH:8]2[CH2:13][CH2:12][O:11][C:9]2=[O:10])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 68745479HCID 68745479, compound

Product 1

HCID 68744317HCID 68744317, compoundYield 77.3%

Reagents, catalysts & solvents 2

HCID 24385Nickel DichlorideCatalystHCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

2-(Cyclohexyl-methylene)-γ-butyrolactone (8.90 g) was added fast to a mixture of nickel(II) chloride (1.76 g) and methanol (30 mL) at room temperature. The obtained reaction mixture was cooled to 0° C., stirred at this temperature for 30 min and then treated portionwise with sodium borohydride (5.60 g). Upon completion of the addition, the mixture was stirred for 1 h at room temperature and then quenched by pouring onto a mixture of ice and 10% aqueous hydrochloric acid. The formed organic phase was separated and the aqueous phase was extracted with ether. The combined organic phases were dried over magnesium sulfate, filtered and concentrated on a rotary evaporator to give 6.96 g (77%) of the title compound.

Workup

  1. customThe obtained reaction mixture
  2. additionUpon completion of the addition
  3. stirringthe mixture was stirred for 1 h at room temperature
  4. customquenched
  5. additionby pouring onto a mixture of ice and 10% aqueous hydrochloric acid
  6. customThe formed organic phase was separated
  7. extractionthe aqueous phase was extracted with ether
  8. dry with materialThe combined organic phases were dried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated on a rotary evaporator

Sources & evidence

ORD record
ord-e6f69e54fe8e4641855e5c43b5dc78e5
Source dataset
uspto-grants-2010_03
Patent number
US07674741B2

Reaction notes

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