Citric Acid → 1-(3,5-Difluoro-2,4-dibenzyloxyphenyl)ethanol

HRID 355410Notes

Reaction equation

HRID 355410 reaction equation
C[Mg]Br.[F:4][C:5]1[C:6]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[C:7]([CH:10]=[C:11]([F:21])[C:12]=1[O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH:8]=[O:9].[CH3:30]COCC.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>>[F:4][C:5]1[C:6]([O:22][CH2:23][C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)=[C:7]([CH:8]([OH:9])[CH3:30])[CH:10]=[C:11]([F:21])[C:12]=1[O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 4

HCID 311Citric AcidHCID 3283Diethyl EtherHCID 189423223,5-Difluoro-2,4-dibenzyloxybenzaldehydeHCID 178418573HCID 178418573, compound

Product 1

HCID 189423411-(3,5-Difluoro-2,4-dibenzyloxyphenyl)ethanol

Conditions

Temperature
0 °C

Procedure

Methylmagnesium bromide (3.0M solution in ether, 1.1 eq) is added to a 0.4M solution of Compound 23 in ether (1.0 eq) at 0° C. The reaction is stirred at 0° C. for 1 hour, then warmed to 20° C. for an additional hour, and poured into 5 volumes of 1M citric acid solution. The resulting solution is extracted with ether (2×), washed with brine, dried over anhydrous MgSO4, and concentrated in vacuo. The residue is purified by chromatography on silica gel (Hex/EtOAc) to yield Compound 24.

Workup

  1. temperaturewarmed to 20° C. for an additional hour
  2. extractionThe resulting solution is extracted with ether (2×)
  3. washwashed with brine
  4. dry with materialdried over anhydrous MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue is purified by chromatography on silica gel (Hex/EtOAc)

Sources & evidence

ORD record
ord-c52af617ab53497e98b637a245416da5
Source dataset
uspto-grants-1998_11
Patent number
US05830912

Reaction notes

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