Sodium Chloride → HCID 10307904, compound

HRID 432063Notes

Reaction equation

HRID 432063 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][CH:5]=1)=[O:3].[Na+].[Cl-].[C:14]1(C(O)(CCCC)CC)C=CC=C[CH:15]=1.CC1C=CC=CC=1C(O)(CC)C>C(Cl)(Cl)Cl>[CH3:11][O:10][C:7]1[CH:8]=[CH:9][C:4]([C:2]([OH:3])([CH2:14][CH3:15])[CH3:1])=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 74764'-MethoxyacetophenoneHCID 10236066HCID 10236066, compoundHCID 10307889α-Ethyl-α,2-dimethylbenzenemethanol

Product 1

HCID 10307904HCID 10307904, compoundYield 85.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

The general procedure A was applied to 4-methoxyacetophenone on a 112 mg (0.73 mmol) scale, using 10 mol % of Compound B (40 mg). The crude product was purified by column chromatography on silica gel (hexanes/EtOAc: 8/2) to give 3 (112 mg, 85.2% yield, 94.0% ee) as an oil: [α]D 20=−13.32 (c 1.8, CHCl3); 1H NMR (CDCl3, 500 MHz) δ 0.77 (dd, J=7.4, 7.4 Hz, 3H), 1.50 (s, 3H), 1.76-1.82 (m, 2H), 3.78 (s, 3H), 6.83-6.86 (m, 2H), 7.31-7.34 (m, 2H) ppm; 13C{1H} NMR (CDCl3, 125 MHz) δ 8.8, 29.9, 37.1, 55.6, 75.0, 113.7, 126.5, 140.3, 158.5 ppm; IR (NaCl) 3444, 2967, 1610, 1300, 1179 cm−1; MS (m/z relative intensity) 180 (M)+ (7), 165 (MCH3)+ (5), 163 (—OH)+ (49), 162 (M-H2O) (15); HMRS calcd for C11H15(—OH)+: 163.1122, found 163.1129.

Workup

  1. customThe crude product was purified by column chromatography on silica gel (hexanes/EtOAc: 8/2)
  2. customto give 3 (112 mg, 85.2% yield, 94.0% ee) as an oil

Sources & evidence

ORD record
ord-0fef1947fefe4eecbfc2fb51af18768e
Source dataset
uspto-grants-2003_12
Patent number
US06660884B2

Reaction notes

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