Hydrochloric Acid → HCID 66777748, compound

HRID 2091104Notes

Reaction equation

HRID 2091104 reaction equation
[CH:1]1([C:7]([C:9]2[O:10][C:11]3[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][O:22][CH3:23])=[CH:15][C:12]=3[C:13]=2[CH3:14])=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[BH4-].[Na+].O.Cl>O1CCCC1.CO>[CH:1]1([CH:7]([C:9]2[O:10][C:11]3[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][O:22][CH3:23])=[CH:15][C:12]=3[C:13]=2[CH3:14])[OH:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 4311764Sodium borohydrideHCID 66777538HCID 66777538, compound2×

Product 1

HCID 66777748HCID 66777748, compoundYield 99.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Cyclohexyl[5-(2-methoxyethoxy)-3-methyl-1-benzofuran-2-yl]methanone (10.3 g) synthesized in the above-mentioned (2) was dissolved in a mixed solvent of tetrahydrofuran (180 mL) and methanol (20 mL). The reaction mixture was ice-cooled, and sodium borohydride (90%, 2.7 g) was added, and the reaction mixture was stirred at room temperature for 2 hr. The reaction mixture was ice-cooled again, water (10 mL) and 1N hydrochloric acid (100 mL) were carefully added, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure to give a crude product (10.3 g) of the title object compound as a pale-yellow oil.

Workup

  1. temperaturecooled
  2. temperaturecooled again
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-07afb8cdd82647d9a60351b907abddc2
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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