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Benzyl Bromide → methyl 3-[(2S)-1-hydroxypropan-2-yl]oxy-5-phenylmethoxy-benzoate

HRID 1175894
Notes
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Reaction equation

HRID 1175894 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:9][C:10]1[CH:11]=[C:12]([CH:17]=[C:18]([O:20][C@@H:21]([CH3:24])[CH2:22][OH:23])[CH:19]=1)[C:13]([O:15][CH3:16])=[O:14].C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C=O)C>[OH:23][CH2:22][C@@H:21]([O:20][C:18]1[CH:17]=[C:12]([CH:11]=[C:10]([O:9][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:19]=1)[C:13]([O:15][CH3:16])=[O:14])[CH3:24]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 7498Benzyl BromideHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 59127187methyl 3-hydroxy-5-[(1S)-2-hydroxy-1-methylethoxy]benzoate

Product 1

HCID 59127113methyl 3-[(2S)-1-hydroxypropan-2-yl]oxy-5-phenylmethoxy-benzoateYield 78.3%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Procedure

Benzyl bromide (1.89 g, 7.20 mmol) was added to a mixture of methyl 3-hydroxy-5-[(1S)-2-hydroxy-1-methylethoxy]benzoate (1.55 g, 6.86 mmol) and potassium carbonate (1.89 g, 0.014 mol) in DMF (16 mL) and the reaction stirred at RT for 20 hours. Ethyl acetate (40 mL) was added and the mixture washed with water (40 mL), saturated sodiumbicarbonate solution (40 mL), brine (40 mL), dried (MgSO4), filtered and the solvent removed in vacuo to give a red oil which was chromatographed on silica, eluting with a gradient of 0-100% ethyl acetate in isohexane, to give the desired compound (1.7 g).

Workup

  1. washthe mixture washed with water (40 mL), saturated sodiumbicarbonate solution (40 mL), brine (40 mL)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. customthe solvent removed in vacuo
  5. customto give a red oil which
  6. customwas chromatographed on silica
  7. washeluting with a gradient of 0-100% ethyl acetate in isohexane

Sources & evidence

ORD record
ord-3fbdaed627674296b5a314a79225d99d
Source dataset
uspto-grants-2010_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07842694B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes