Potassium Carbonate → HCID 18320531, compound

HRID 1735651Notes

Reaction equation

HRID 1735651 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:15]([O:27][CH3:28])=[C:16]2[CH:23]3[CH2:24][CH:19]4[CH2:20][C:21]([Cl:26])([CH2:25][CH:17]2[CH2:18]4)[CH2:22]3)[CH:5]=[C:6]([O:8]C(=O)C(C)(C)C)[CH:7]=1.C([O-])([O-])=O.[K+].[K+]>CO>[Cl:1][C:2]1[CH:3]=[C:4]([C:15]([O:27][CH3:28])=[C:16]2[CH:17]3[CH2:18][CH:19]4[CH2:20][C:21]([Cl:26])([CH2:22][CH:23]2[CH2:24]4)[CH2:25]3)[CH:5]=[C:6]([OH:8])[CH:7]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 18320519HCID 18320519, compound

Product 1

HCID 18320531HCID 18320531, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Crude pivaloate 15 was hydrolyzed at room temperature with K2CO3 (1.45 g, 10.5 mmol) in 10 ml methanol. Evaporation of methanol, followed by standard workup and purification (silica gel, 30% EtOAc/hexanes) afforded 1.095 g (63% over 2 steps) of a slightly yellow oil which solidified upon standing. Trituration of the solid produced white crystalline enol ether phenol 16, mp 130° C.

Workup

  1. customEvaporation of methanol
  2. customfollowed by standard workup and purification (silica gel, 30% EtOAc/hexanes)
  3. customafforded 1.095 g (63% over 2 steps) of a slightly yellow oil which

Sources & evidence

ORD record
ord-055e5107623f4d56ae599d68f8ab2727
Source dataset
uspto-grants-1996_07
Patent number
US05538847

Reaction notes

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