Sodium borohydride → HCID 90389980, compound

HRID 59779Notes

Reaction equation

HRID 59779 reaction equation
[C:1]1([CH:7]2[CH2:16][CH2:15][C:14]3[C:9](=[CH:10][CH:11]=[C:12]([O:17][CH:18]4[CH2:23][CH2:22][C:21](=[O:24])[CH2:20][CH2:19]4)[CH:13]=3)[O:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[BH4-].[Na+]>C(O)C>[C:1]1([CH:7]2[CH2:16][CH2:15][C:14]3[C:9](=[CH:10][CH:11]=[C:12]([O:17][CH:18]4[CH2:23][CH2:22][CH:21]([OH:24])[CH2:20][CH2:19]4)[CH:13]=3)[O:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 903901554-(2-Phenyl-chroman-6-yloxy)-cyclohexanone

Product 1

HCID 90389980HCID 90389980, compoundYield 96.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

500 mg of 4-(2-phenyl-chroman-6-yloxy)-cyclohexanone (1.6 mmol) were dissolved at 0° C. in 2.5 ml of ethanol. 30 mg of sodium borohydride (0.78 mmol) were added in portions, and stirring at room temperature was continued for 2 h. The solvent was removed under reduced pressure and the residue separated between saturated aqueous sodium hydrogencarbonate solution and dichloromethane. The aqueous layer was extracted with dichloromethane. The combined organic layers were dried with sodium sulfate and filtered, and volatile components removed under reduced pressure. 500 mg of the title compound were obtained as a pale yellow solid.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue separated between saturated aqueous sodium hydrogencarbonate solution and dichloromethane
  3. extractionThe aqueous layer was extracted with dichloromethane
  4. dry with materialThe combined organic layers were dried with sodium sulfate
  5. filtrationfiltered
  6. customvolatile components removed under reduced pressure

Sources & evidence

ORD record
ord-bad77bf8f38c4ed28ed07e45a81f81f7
Source dataset
uspto-grants-2016_09
Patent number
US09440941B2

Reaction notes

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