Potassium Carbonate → HCID 18320531, compound

HRID 370306Notes

Reaction equation

HRID 370306 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-331fd00204674f65991732c124c1e936
Source dataset
uspto-grants-2000_10
Patent number
US06140495

Reaction notes

Loading…