HCID 1729098, compound → HCID 86632590, compound

HRID 660785Notes

Reaction equation

HRID 660785 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[O:10][S:11]([CH3:14])(=[O:13])=[O:12].[Li+].[BH4-]>C1COCC1.CCOC(C)=O.Cl>[OH:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[O:10][S:11]([CH3:14])(=[O:13])=[O:12]

Participants

6

Reactant 2

HCID 1729098HCID 1729098, compoundHCID 4148881Lithium borohydride

Product 1

HCID 86632590HCID 86632590, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
45 °C

Procedure

To a solution of 2-methanesulfonyloxybenzoic acid methyl ester (1.0 g, 4.3 mmol) in THF (10 mL) is added LiBH4 (375 mg, 17.2 mmol) in portions. The mixture is heated at 45° C. for 2 h then at 60° C. for 2 h. The mixture is diluted with EtOAc and ice and 1N HCl is added. The organic phase is separated and washed with 1N HCl and brine then dried over magnesium sulfate. The solvent is removed under reduced pressure to give the title compound as a solid.

Workup

  1. additionis added
  2. customThe organic phase is separated
  3. washwashed with 1N HCl and brine
  4. dry with materialthen dried over magnesium sulfate
  5. customThe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-76f1efb56acf4e029b947184db0f5904
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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