Ethanol → 1-Acetylamino-11-benzyloxy-1,1-diethoxycarbonylundecane

Reaction equation

[C:1]([OH:7])(=[O:6])[CH2:2][C:3]([OH:5])=[O:4].C([CH:10](CC)[C:11]([NH2:13])=[O:12])C.[O-][CH2:17][CH3:18].[Na+].[CH2:20]([O:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37]I)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[CH2:39](O)[CH3:40]>>[C:11]([NH:13][C:2]([C:1]([O:7][CH2:17][CH3:18])=[O:6])([C:3]([O:5][CH2:39][CH3:40])=[O:4])[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][O:27][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)(=[O:12])[CH3:10]

Participants

Reactant 4

HCID 702Ethanol

HCID 2723922Sodium ethoxide

HCID 137127691-Benzyloxy-10-iododecane

HCID 22466969Diethyl acetamide malonate

Product 1

HCID 224670111-Acetylamino-11-benzyloxy-1,1-diethoxycarbonylundecaneYield 89.7%

Procedure

Anhydrous ethanol (10.5 ml) and diethylacetamide malonate (2661 mg, 12.25 mmols) were added to sodium ethoxide (834 mg, 12.25 mmols). After stirring for 10 minutes, 1-benzyloxy-10-iododecane (Compound q-1) (2661 mg, 12.25 mmols) was added to the mixture. The mixture was heated to reflux for 4 hours and concentrated in vacuo. Chloroform (200 ml) and water (100 ml) were added to the residue for separation. The organic layer was washed with saturated sodium chloride aqueous solution (100 ml), dried over anhydrous sodium sulfate and then concentrated. The residue was purified by silica gel column chromatography (300 ml, hexane:ethyl acetate=4:1) to give Compound (r-2) (5080 mg, yield: 89.7%).