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Sodium borohydride → Methyl 1-(4-((3-(hydroxy(phenyl)methyl)phenoxy)-methyl)phenyl)cyclopropanecarboxylate

HRID 332682
Notes
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Reaction equation

HRID 332682 reaction equation
[C:1]([C:9]1[CH:10]=[C:11]([CH:27]=[CH:28][CH:29]=1)[O:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2([C:23]([O:25][CH3:26])=[O:24])[CH2:22][CH2:21]2)=[CH:16][CH:15]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>CO>[OH:8][CH:1]([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:9]1[CH:10]=[C:11]([CH:27]=[CH:28][CH:29]=1)[O:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2([C:23]([O:25][CH3:26])=[O:24])[CH2:22][CH2:21]2)=[CH:16][CH:15]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 4311764Sodium borohydride2×HCID 71093088Methyl 1-(4-((3-benzoylphenoxy)methyl)phenyl)cyclopropanecarboxylate

Product 1

HCID 71113166Methyl 1-(4-((3-(hydroxy(phenyl)methyl)phenoxy)-methyl)phenyl)cyclopropanecarboxylateYield 98.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of methyl 1-(4-((3-benzoylphenoxy)methyl)phenyl)-cyclopropanecarboxylate (1.85 g, 4.787 mmol) in methanol (22.6 mL) at 0° C. under an atmosphere of nitrogen, was added sodium borohydride (0.181 g, 4.787 mmol) in one portion. The reaction mixture was stirred at 0° C. for 1 hour and then allowed to warm to room temperature. After stirring for 40 minutes, the reaction was cooled to 0° C., and additional sodium borohydride (0.091 g, 2.380 mmol) was added. The reaction mixture was allowed to warm to room temperature and stirred for 30 minutes. The reaction was quenched with water (3.5 mL), filtered to remove insoluble material, and then concentrated under reduced pressure. Water was added to the residue and extracted with ethyl acetate (×2). The combined organic extracts were washed with 10% aqueous potassium carbonate (×2), brine, dried (magnesium sulfate), filtered, and concentrated under reduced pressure to afford the title compound as a red oil (1.824 g, 98%). The material was used directly in the next step with no further purification.

Workup

  1. temperatureto warm to room temperature
  2. stirringAfter stirring for 40 minutes
  3. temperaturethe reaction was cooled to 0° C.
  4. temperatureto warm to room temperature
  5. stirringstirred for 30 minutes
  6. customThe reaction was quenched with water (3.5 mL)
  7. filtrationfiltered
  8. customto remove insoluble material
  9. concentrationconcentrated under reduced pressure
  10. additionWater was added to the residue
  11. extractionextracted with ethyl acetate (×2)
  12. washThe combined organic extracts were washed with 10% aqueous potassium carbonate (×2), brine
  13. dry with materialdried (magnesium sulfate)
  14. filtrationfiltered
  15. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b2b6b56825324c22938c087d014c2ed9
Source dataset
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08877774B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes