Chloromethyl Methyl Ether → 1,5-Diphenyl-3-((methoxy)methoxy)pentane

HRID 1078108Notes

Reaction equation

HRID 1078108 reaction equation
[C:1]1([CH2:7][CH2:8][CH:9]([OH:18])[CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(C(C)C)C(C)C)C.[CH3:28][O:29][CH2:30]Cl>ClCCl.C(OCC)(=O)C>[C:12]1([CH2:11][CH2:10][CH:9]([O:18][CH2:28][O:29][CH3:30])[CH2:8][CH2:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

6

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 81531DiisopropylethylamineHCID 128385101,5-Diphenylpentan-3-ol

Product 1

HCID 194310041,5-Diphenyl-3-((methoxy)methoxy)pentaneYield 91.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 101 mg (0.42 mmol) of 1,5-diphenyl-3-pentanol, 0.18 ml (1.0 mmol) of ethyldiisopropylamine, and 0.063 ml (0.84 mmol) of chloromethyl methyl ether in 1 ml of dichloromethane was allowed to stand for 16 h. The resulting solution was taken up in ethyl acetate, washed sequentially with 10% aqueous citric acid, water, and saturated sodium bicarbonate, dried over Na2SO4, and concentrated in vacuo. Flash chromatography using 10% ethyl acetate in hexane gave 109 mg (92%) of the desired compound (Rf 0.51, 25% ethyl acetate in hexane) as an oil. 1H NMR (CDCl3) δ1.88 (m, 4H), 2.70 (m, 4H), 3.44 (s, 3H), 3.64 (pentet, J=6 Hz, 1H), 4.70 (s, 2H), 7.15-7.3 (m, 10H). Mass spectrum (M+NH4)+ =302.

Workup

  1. washwashed sequentially with 10% aqueous citric acid, water, and saturated sodium bicarbonate
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-66f469dc5b0f4f39be47f5c6a5353539
Source dataset
uspto-grants-1996_08
Patent number
US05545750

Reaction notes

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