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

HRID 1821932Notes

Reaction equation

HRID 1821932 reaction equation
[C:1]([O:5][C:6]([C:8]1[CH:12]=[CH:11][N:10]([CH2:13][CH:14]([O:31]C(=O)C)[CH2:15][O:16][C:17]2[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])=[CH:19][CH:18]=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[CH:12]=[CH:11][N:10]([CH2:13][CH:14]([OH:31])[CH2:15][O:16][C:17]2[CH:18]=[CH:19][C:20]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])=[CH:21][CH:22]=2)[CH:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 12992899tert-Butyl-1-[2-acetoxy-3-(4-octylphenoxy)propyl]pyrrole-3-carboxylate

Product 1

HCID 12992900tert-Butyl-1-[2-hydroxy-3-(4-octylphenoxy)propyl]pyrrole-3-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.104 g (0.221 mmol) tert-butyl-1-[2-acetoxy-3-(4-octylphenoxy)propyl]pyrrole-3-carboxylate is dissolved in 10 ml absolute methanol, mixed with 0.88 ml (0.440 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

  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

Sources & evidence

ORD record
ord-b81a4d542f6940efaa0edc300f6c931b
Source dataset
uspto-grants-2009_10
Patent number
US07608633B2

Reaction notes

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