Sodium Methoxide → tert-Butyl-1-[2-hydroxy-3-(4-octylphenoxy)propyl]indole-3-carboxylate
Reaction equation
[C:1]([O:5][C:6]([C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]([CH2:17][CH:18]([O:35]C(=O)C)[CH2:19][O:20][C:21]2[CH:26]=[CH:25][C:24]([CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])=[CH:23][CH:22]=2)[CH:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C[O-].[Na+]>CO>[C:1]([O:5][C:6]([C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]([CH2:17][CH:18]([OH:35])[CH2:19][O:20][C:21]2[CH:22]=[CH:23][C:24]([CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])=[CH:25][CH:26]=2)[CH:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]Participants
4
Procedure
0.293 g (0.562 mmol) tert-butyl-1-[2-acetoxy-3-(4-octylphenoxy)propyl]indole-3-carboxylate is dissolved in 20 ml absolute methanol, mixed with 2.24 ml (1.12 mmol) of a 0.5M sodium methanolate solution and stirred at room temperature for 15 min. Following concentration to half the volume on the rotary evaporator, the batch is diluted with diethyl ether. Washing of the organic phase with semi-saturated and with saturated NaCl solution, drying on sodium sulfate, filtration and reconcentration on the rotary evaporator yield the product as a yellowish oil.
Workup
- concentrationconcentration to half the volume
- customon the rotary evaporator
- additionthe batch is diluted with diethyl ether
- washWashing of the organic phase with semi-saturated and with saturated NaCl solution
- customdrying on sodium sulfate, filtration and reconcentration on the rotary evaporator
Sources & evidence
- ORD record
- ord-a0f0165f5c0d4d37b7274e4e094c4e18
- Source dataset
- uspto-grants-2009_10
- Patent number
- US07608633B2
Reaction notes
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