Hydrochloric Acid → HCID 57541968, compound

HRID 2422234Notes

Reaction equation

HRID 2422234 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][O:16][C:17]3[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][C:25]([O:27][CH3:28])=[O:26])=[CH:19][CH:18]=3)[CH:10]=2)[CH:6]=[CH:7][CH:8]=1)=[O:2].[BH4-].[Na+].Cl>CO.O1CCCC1>[OH:2][CH2:1][C:3]1[CH:4]=[C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][O:16][C:17]3[CH:18]=[CH:19][C:20]([CH2:23][CH2:24][C:25]([O:27][CH3:28])=[O:26])=[CH:21][CH:22]=3)[CH:10]=2)[CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 57541970HCID 57541970, compound

Product 1

HCID 57541968HCID 57541968, compoundYield 101.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl 4-[(3′-formyl-[1,1′-biphenyl]-3-yl) methoxy]benzenepropanoate (0.80 g, 2.1 mmol) in methanol (5 mL) and tetrahydrofuran (2 mL) was ice-cooled, and sodium borohydride (81 mg, 2.1 mmol) was added. The mixture was stirred under ice-cooling for 30 min. The reaction mixture was added to 0.2N hydrochloric acid (11 mL), and the mixture was extracted with ethyl acetate. The extract was washed with water and concentrated under reduced pressure to give the title compound 0.80 g (quantitative). oil.

Workup

  1. temperaturecooled
  2. temperaturecooling for 30 min
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with water
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b170374341fd4563b119cc4efa7fcdb3
Source dataset
uspto-grants-2011_06
Patent number
US07960369B2

Reaction notes

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