Methanol → HCID 69782806, compound

HRID 2415458Notes

Reaction equation

HRID 2415458 reaction equation
[F:1][C:2]1[CH:23]=[CH:22][C:5]([CH2:6][O:7][C:8]2[CH:16]=[CH:15][C:11]([C:12](O)=[O:13])=[C:10]([CH2:17][C:18]([O:20][CH3:21])=[O:19])[CH:9]=2)=[CH:4][CH:3]=1.CO>C1COCC1>[CH3:21][O:20][C:18](=[O:19])[CH2:17][C:10]1[CH:9]=[C:8]([O:7][CH2:6][C:5]2[CH:22]=[CH:23][C:2]([F:1])=[CH:3][CH:4]=2)[CH:16]=[CH:15][C:11]=1[CH2:12][OH:13]

Participants

4

Reactant 2

HCID 887MethanolHCID 22641904HCID 22641904, compound

Product 1

HCID 69782806HCID 69782806, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The 4-(4-fluoro-benzyloxy)-2-methoxycarbonylmethyl-benzoic acid (1.15 g, 3.6 mmol) is solved in THF (28 mL) and borane-dimethylsulfide complex is added (0.69 mL, 7.26 mmol) at 0° C. The reaction is stirred for 2 hours at room temperature and more borane-dimethylsulfide complex (0.69 mL, 7.26 mmol) is added at 0° C. The reaction mixture was stirred at room temperature for 7 h. Methanol was added very slowly and the mixture stirred 20 min. Filtration and concentration in a rotatory evaporator left a solid that was purified through a Silica-gel column using hexane/ethyl acetate 3/1 to 1/2 as eluents (0.927 g, 71.4%). MS: m/e=304 (M+).

Workup

  1. additionborane-dimethylsulfide complex is added (0.69 mL, 7.26 mmol) at 0° C
  2. additionmore borane-dimethylsulfide complex (0.69 mL, 7.26 mmol) is added at 0° C
  3. stirringThe reaction mixture was stirred at room temperature for 7 h
  4. stirringthe mixture stirred 20 min
  5. filtrationFiltration and concentration
  6. customin a rotatory evaporator
  7. waitleft a solid
  8. customthat was purified through a Silica-gel column

Sources & evidence

ORD record
ord-c5612a20ce1e48d58bcc446c3619c72b
Source dataset
uspto-grants-2004_11
Patent number
US06818774B2

Reaction notes

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