tert-Butanol → N-(7-(1,2-Dihydroxyethyl)-3-(4-isopropylphenyl)-4,6-dimethyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide

HRID 2376446Notes

Reaction equation

HRID 2376446 reaction equation
[C:1]([OH:5])([CH3:4])([CH3:3])C.[CH:6]([C:9]1[CH:14]=[CH:13][C:12]([CH:15]2[C:19]3[C:20]([CH3:35])=[C:21]([NH:27][C:28](=[O:34])[CH2:29][C:30]([CH3:33])([CH3:32])[CH3:31])[C:22]([CH3:26])=C(C=C)[C:18]=3[O:17][CH2:16]2)=[CH:11][CH:10]=1)([CH3:8])[CH3:7].S([O-])([O-])=[O:37].[Na+].[Na+]>O.C1COCC1>[OH:5][CH:1]([C:4]1[C:18]2[O:17][CH2:16][CH:15]([C:12]3[CH:13]=[CH:14][C:9]([CH:6]([CH3:7])[CH3:8])=[CH:10][CH:11]=3)[C:19]=2[C:20]([CH3:35])=[C:21]([NH:27][C:28](=[O:34])[CH2:29][C:30]([CH3:32])([CH3:33])[CH3:31])[C:22]=1[CH3:26])[CH2:3][OH:37]

Participants

6

Reactant 3

HCID 6386tert-ButanolHCID 24437Sodium SulfiteHCID 23113980N-(3-(4-Isopropylphenyl)-4,6-dimethyl-7-vinyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide

Product 1

HCID 23114170N-(7-(1,2-Dihydroxyethyl)-3-(4-isopropylphenyl)-4,6-dimethyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamideYield 77%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of AD-mix β (4.62 g) in a mixed solvent of water (15 mL), tert-butanol (15 mL) and THF (15 mL) was added with ice-cooling N-(3-(4-isopropylphenyl)-4,6-dimethyl-7-vinyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide (670 mg, 1.65 mmol) obtained in Example 83 and the reaction mixture was stirred at 80° C. for 3 hours. To the reaction solution were added water and sodium sulfite and the resulting mixture was stirred at room temperature for 30 minutes. The product was extracted with ethyl acetate, and the organic layer was washed with water and saturated brine, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:20) to obtain 558 mg (yield: 77%) of the title compound. Melting point: 159-161° C. (hexane-ethyl acetate).

Workup

  1. stirringthe resulting mixture was stirred at room temperature for 30 minutes
  2. extractionThe product was extracted with ethyl acetate
  3. washthe organic layer was washed with water and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:20)

Sources & evidence

ORD record
ord-d7b63e8492cd431b9fd1eed5befc1fc2
Source dataset
uspto-grants-2008_12
Patent number
US07465815B2

Reaction notes

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