1-(Chloromethoxy)-2-methoxyethane → N-Benzyloxycarbonyl-O-(2-methoxyethoxymethyl)ethanolamine
Reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][OH:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.[CH3:24][O:25][CH2:26][CH2:27][O:28][CH2:29]Cl>ClCCl>[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][O:14][CH2:24][O:25][CH2:26][CH2:27][O:28][CH3:29])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Participants
Procedure
To a cooled (0° C.) solution of N-benzyloxycarbonyl-ethanolamine (12.03 g, 61.6 mmol) in dry dichloromethane (50 ml) was added diisopropylethylamine (32.2 ml, 184.9 mmol) and 2-methoxyethoxymethyl chloride (16.9 ml, 147.9 mmol) with stirring. The mixture was allowed to warm to room temperature then stirred for a further 3 hours. The solvent was removed under reduced pressure and the residue was taken up in ethyl acetate and washed successively with 1M hydrochloric acid, sat. aq. sodiumhydrogen carbonate and brine. The organic phase was dried over magnesium sulphate, filtered and evaporated to porvide the title compound as a orange/yellow oil which was used without further purification. 1H--NMR; δ(CDCI3), 7.35 (5H, m), 5.45 (1H, m), 5.11 (2H, s), 4.72 (2H, s), 3.67 (4H, m), 3.55 (2H, m) and 3.38 (5H, m).
Workup
- stirringthen stirred for a further 3 hours
- customThe solvent was removed under reduced pressure
- washwashed successively with 1M hydrochloric acid, sat. aq. sodiumhydrogen carbonate and brine
- dry with materialThe organic phase was dried over magnesium sulphate
- filtrationfiltered
- customevaporated
- customwas used without further purification
Sources & evidence
- ORD record
- ord-79a29c4634cf420bb99bf54aa730b551
- Source dataset
- uspto-grants-1999_02
- Patent number
- US05866717
Reaction notes
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