Sodium Methoxide → tert-Butyl-1-[2-hydroxy-3-(4-octylphenoxy)propyl]indole-2-carboxylate

HRID 1821937Notes

Reaction equation

HRID 1821937 reaction equation
[C:1]([O:5][C:6]([C:8]1[N:9]([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)[C:10]2[C:15]([CH:16]=1)=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:7])([CH3:4])([CH3:3])[CH3:2].C[O-].[Na+]>CO>[C:1]([O:5][C:6]([C:8]1[N:9]([CH2:17][CH:18]([OH:35])[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)[C:10]2[C:15]([CH:16]=1)=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 11526497tert-Butyl-1-[2-acetoxy-3-(4-octylphenoxy)propyl]indole-2-carboxylate

Product 1

HCID 11627108tert-Butyl-1-[2-hydroxy-3-(4-octylphenoxy)propyl]indole-2-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.213 g (0.408 mmol) tert-butyl-1-[2-acetoxy-3-(4-octylphenoxy)propyl]indole-2-carboxylate is dissolved in 10 ml absolute methanol, mixed with 1.64 ml (0.82 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 leave as a crude product a yellowish oil which is purified on silica gel by means of column chromatography (flow agent: petroleum ether/ethyl acetate 95:5) and yields the product as a yellowish oil.

Workup

  1. concentrationconcentration to half the volume
  2. customon the rotary evaporator
  3. additionthe batch is diluted with diethyl ether
  4. washWashing of the organic phase with semi-saturated and with saturated NaCl solution
  5. customdrying on sodium sulfate, filtration and reconcentration on the rotary evaporator
  6. customleave as a crude product a yellowish oil which
  7. customis purified on silica gel by means of column chromatography (flow agent: petroleum ether/ethyl acetate 95:5)

Sources & evidence

ORD record
ord-5a8051699af14c68b28c04d039796d85
Source dataset
uspto-grants-2009_10
Patent number
US07608633B2

Reaction notes

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