Water → HCID 57424217, compound

HRID 1869865Notes

Reaction equation

HRID 1869865 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[C:5](Cl)(=[O:7])[CH3:6].[Br:9][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[O:16][C:15]([CH2:22][CH3:23])([CH2:20][CH3:21])[CH2:14][C:13]2([CH3:25])[CH3:24].O>ClCCl>[C:5]([C:18]1[CH:19]=[C:10]([Br:9])[CH:11]=[C:12]2[C:17]=1[O:16][C:15]([CH2:22][CH3:23])([CH2:20][CH3:21])[CH2:14][C:13]2([CH3:24])[CH3:25])(=[O:7])[CH3:6]

Participants

6

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 21107217HCID 21107217, compound2×

Product 1

HCID 57424217HCID 57424217, compoundYield 84.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A stirred, cooled (ice bath) suspension of aluminum chloride (1.1 g, 8.38 mmol) in anhydrous dichloromethane (20 mL) was treated with acetyl chloride (0.6 mL, 8.38 mmol). After 5 minutes, a solution of 6-bromo-2,2-diethyl-4,4-dimethyl chroman (Intermediate 25, 1.66 g, 5.59 mmol) in dichloromethane was added. The reaction mixture was stirred for 1 h. The reaction mixture was then poured into water and extracted with diethyl ether (×2). The combined organic phase was washed with saturated aqueous sodium bicarbonate solution, dried over anhydrous sodium sulfate, filtered and evaporated in vacuo to a residue which was subjected to flash column chromatography over silica gel (230-400 mesh) using 10% ethyl acetate in hexane as the eluent to afford the title compound as an oil (1.6 g, 84%).

Workup

  1. temperatureA stirred, cooled
  2. extractionextracted with diethyl ether (×2)
  3. washThe combined organic phase was washed with saturated aqueous sodium bicarbonate solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo to a residue which

Sources & evidence

ORD record
ord-4f6ce90fda504f9e9ac95148eed7bcfa
Source dataset
uspto-grants-2009_12
Patent number
US07638648B2

Reaction notes

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