(Dimethyl sulfide)trihydroboron → HCID 24813623, compound

HRID 658242Notes

Reaction equation

HRID 658242 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:15]=[C:16]([C:18]([O:20][CH3:21])=[O:19])[CH:17]=1)[C:12](O)=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B.CSC>C1COCC1>[CH2:1]([O:8][C:9]1[CH:17]=[C:16]([CH:15]=[C:11]([CH2:12][OH:13])[CH:10]=1)[C:18]([O:20][CH3:21])=[O:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 12423031(Dimethyl sulfide)trihydroboron2×HCID 214406211-Methyl 5-(phenylmethoxy)-1,3-benzenedicarboxylate

Product 1

HCID 24813623HCID 24813623, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(benzyloxy)-5-(methoxycarbonyl)benzoic acid (1 eq.) from the previous step in THF (0.2 M) at 0° C. was added borane-dimethylsulfide (1.5 eq.) and stirred at rt for 18 h. Additional borane-dimethylsulfide (3 eq.) was added and the reaction was stirred for another 2 h at rt. The reaction was slowly quenched with methanol and then concentrated in vacuo. The residue was diluted with EtOAc and washed with saturated aqueous NaHCO3 solution, and brine. The organic extract was dried over MgSO4 and concentrated in vacuo to give the title compound.

Workup

  1. stirringthe reaction was stirred for another 2 h at rt
  2. customThe reaction was slowly quenched with methanol
  3. concentrationconcentrated in vacuo
  4. additionThe residue was diluted with EtOAc
  5. washwashed with saturated aqueous NaHCO3 solution, and brine
  6. extractionThe organic extract
  7. dry with materialwas dried over MgSO4
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ed9f066418ff4d6b9c4acd0950583dd1
Source dataset
uspto-grants-2011_12
Patent number
US08076359B2

Reaction notes

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