Acetic Acid → HCID 11652636, compound

HRID 1026186Notes

Reaction equation

HRID 1026186 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10](=[O:23])[CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][C:14]=1[O:21][CH3:22].[BH4-].[Na+].C(O)(=O)C>C(O)CC>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[CH:10]([OH:23])[CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][C:14]=1[O:21][CH3:22]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 4311764Sodium borohydride2×HCID 59420442HCID 59420442, compound

Product 1

HCID 11652636HCID 11652636, compound

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Procedure

1-(2-hydroxy-5-methoxyphenyl)-3-(2′,4′-dimethoxyphenyl)-1-propanone (6) (5 mg) was dissolved in 1-propanol (1 ml), followed by the addition of sodium borohydride (2 mg) and the mixture was allowed to react at room temperature for 5 hours. Upon completion of the reaction, 20% acetic acid (0.2 ml) was added to neutralize the excess sodium borohydride. The reaction mixture was then separated on a pre-packed C18 column eluting with a MeOH/H2O gradient to provide 1-(2-hydroxy-5-methoxyphenyl)-3-(2′,4′-dimethoxyphenyl)-1-propanol (7).

Workup

  1. customto react at room temperature for 5 hours
  2. additionwas added
  3. customThe reaction mixture was then separated on a pre-packed C18 column
  4. washeluting with a MeOH/H2O gradient

Sources & evidence

ORD record
ord-e23f39290b0d4a12871a0ff2a86db952
Source dataset
uspto-grants-2014_05
Patent number
US08729136B2

Reaction notes

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