Hydrochloric Acid → HCID 66778469, compound

HRID 2091430Notes

Reaction equation

HRID 2091430 reaction equation
[CH:1]1([C:7]([C:9]2[C:13]3[CH:14]=[CH:15][C:16]([O:18][CH3:19])=[CH:17][C:12]=3[O:11][C:10]=2[CH3:20])=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CO.[BH4-].[Na+].Cl>O1CCCC1>[CH:1]1([CH:7]([C:9]2[C:13]3[CH:14]=[CH:15][C:16]([O:18][CH3:19])=[CH:17][C:12]=3[O:11][C:10]=2[CH3:20])[OH:8])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 4311764Sodium borohydrideHCID 66778158Cyclohexyl(6-methoxy-2-methyl-1-benzofuran-3-yl)methanone

Product 1

HCID 66778469HCID 66778469, compoundYield 76.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of cyclohexyl(6-methoxy-2-methyl-1-benzofuran-3-yl)methanone (1.18 g) synthesized above, methanol (1 mL) and tetrahydrofuran (10 mL) was added sodium borohydride (246 mg) at 0° C., and the mixture was stirred for 30 min. 1N Hydrochloric acid was added to quench the reaction, the organic solvent was evaporated in an evaporator, and the residue was extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure to give the title object compound (906 mg, 76%) as a pale-yellow oil.

Workup

  1. customto quench
  2. customthe reaction
  3. customthe organic solvent was evaporated in an evaporator
  4. extractionthe residue was extracted with ethyl acetate
  5. washThe extract was washed with saturated brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d895591bd51a4167b99dafc2b5bf77d8
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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