Sodium borohydride → HCID 118114326, compound

HRID 2284854Notes

Reaction equation

HRID 2284854 reaction equation
[C:1]([C:9]1[CH:25]=[CH:24][C:12]([O:13][CH2:14][C:15]2[O:19][C:18]([C:20]([O:22][CH3:23])=[O:21])=[CH:17][CH:16]=2)=[CH:11][CH:10]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>CO.C1COCC1>[OH:8][CH:1]([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:9]1[CH:25]=[CH:24][C:12]([O:13][CH2:14][C:15]2[O:19][C:18]([C:20]([O:22][CH3:23])=[O:21])=[CH:17][CH:16]=2)=[CH:11][CH:10]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 4378040HCID 4378040, compound

Product 1

HCID 118114326HCID 118114326, compoundYield 96.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of methyl 5-((4-benzoylphenoxy)methyl)furan-2-carboxylate (330 mg, 1.0 mmol) in methanol (5 mL) and THF (5 mL) was cooled to 0° C. NaBH4 (58 mg, 1.53 mmol) was added in one portion and the reaction was stirred at 0° C. for 2 hours. The reaction was quenched by addition of water (0.75 mL). The mixture was stirred for 10 minutes and the majority of the solvent was removed in vacuo. The residue was partitioned between EtOAc and water and the aqueous phase was extracted twice with EtOAc. The combined organic phases were washed with brine, dried over MgSO4, filtered and the solvent was removed in vacuo to give the title compound (325 mg, 96.1%) as a yellow oil.

Workup

  1. customThe reaction was quenched by addition of water (0.75 mL)
  2. stirringThe mixture was stirred for 10 minutes
  3. customthe majority of the solvent was removed in vacuo
  4. customThe residue was partitioned between EtOAc and water
  5. extractionthe aqueous phase was extracted twice with EtOAc
  6. washThe combined organic phases were washed with brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-c9e0a7b56ac5477f8aa60408072c2b69
Source dataset
uspto-grants-2015_09
Patent number
US09145409B2

Reaction notes

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