Carbon Tetrachloride → 3-(4-Methoxytetrahydropyran-4-yl)benzyl chloride

HRID 1034300Notes

Reaction equation

HRID 1034300 reaction equation
[C:1]([Cl:5])(Cl)(Cl)Cl.[CH3:6][O:7][C:8]1([C:14]2[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=2)CO)[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1.CN(P(N(C)C)(N(C)C)=O)C>C1COCC1>[CH3:6][O:7][C:8]1([C:14]2[CH:21]=[C:20]([CH:19]=[CH:16][CH:15]=2)[CH2:1][Cl:5])[CH2:9][CH2:10][O:11][CH2:12][CH2:13]1

Participants

5

Reactant 3

HCID 5943Carbon TetrachlorideHCID 12679HexamethylphosphoramideHCID 542317503-(4-Methoxytetrahydropyran-4-yl)benzyl alcohol

Product 1

HCID 190236933-(4-Methoxytetrahydropyran-4-yl)benzyl chlorideYield 81%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Carbon tetrachloride (30.3 g, 198 mmol) was added dropwise over 20 minutes to a solution of 3-(4-methxytetrahydropyran-4-yl)benzyl alcohol from Step 4 (29.3 g, 132 mmol) and HMPA (32.2 g, 198 mmol) in THF (400 mL) at 0°-5° C. The mixture was stirred for 10 minutes and then concentrated. Excess Et2O was added and the mixture filtered through a celite pad. The filtrate was concentrated and chromatographed on silica gel using 20% EtOAc in hexane as eluent to obtain 24 g (81%) of the title compound as an oil.

Workup

  1. concentrationconcentrated
  2. additionExcess Et2O was added
  3. filtrationthe mixture filtered through a celite pad
  4. concentrationThe filtrate was concentrated
  5. customchromatographed on silica gel using 20% EtOAc in hexane as eluent

Sources & evidence

ORD record
ord-ccbc0de6ec2e4886bb0edc46d59cb7c1
Source dataset
uspto-grants-1994_05
Patent number
US05314900

Reaction notes

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