Lithium Hydroxide → HCID 9931840, compound

HRID 1602690Notes

Reaction equation

HRID 1602690 reaction equation
[C:1]12([C:11]3[CH:12]=[C:13]([C:19]4([CH3:32])[C:23]5[CH:24]=[CH:25][C:26]([C:28]([O:30]C)=[O:29])=[CH:27][C:22]=5[O:21][CH2:20]4)[CH:14]=[CH:15][C:16]=3[O:17][CH3:18])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[OH-].[Na+].[OH-].[Li+]>>[C:1]12([C:11]3[CH:12]=[C:13]([C:19]4([CH3:32])[C:23]5[CH:24]=[CH:25][C:26]([C:28]([OH:30])=[O:29])=[CH:27][C:22]=5[O:21][CH2:20]4)[CH:14]=[CH:15][C:16]=3[O:17][CH3:18])[CH2:10][CH:5]3[CH2:4][CH:3]([CH2:9][CH:7]([CH2:6]3)[CH2:8]1)[CH2:2]2

Participants

4

Reactant 3

HCID 3939Lithium HydroxideHCID 14798Sodium HydroxideHCID 15385050HCID 15385050, compound

Product 1

HCID 9931840HCID 9931840, compound

Procedure

A mixture of methyl 3-[3-(1-adamantyl)-4-methoxyphenyl]-3-methyl-2H-1-benzofuran-6-carboxylate (62 mg, 0.14 mmol), sodium hydroxide (0.012 g, 0.3 mmol) and lithium hydroxide (0.012 g, 0.28 mmol) is refluxed for 6 h. The mixture is concentrated on a rotary evaporator under vacuum at 40° C. 10 ml of water and 10 ml of ethyl acetate are added. The mixture is acidified with concentrated hydrochloric acid solution to pH=1. After separation of the phases by settling, the organic phase is washed twice with 10 ml of water, dried over magnesium sulphate and concentrated on a rotary evaporator under vacuum at 40° C. The product is purified by flash chromatography on a column of silica (50% CH2Cl2 50% EtOAc).

Workup

  1. temperatureis refluxed for 6 h
  2. concentrationThe mixture is concentrated on a rotary evaporator under vacuum at 40° C
  3. addition10 ml of water and 10 ml of ethyl acetate are added
  4. customAfter separation of the phases
  5. washthe organic phase is washed twice with 10 ml of water
  6. dry with materialdried over magnesium sulphate
  7. concentrationconcentrated on a rotary evaporator under vacuum at 40° C
  8. customThe product is purified by flash chromatography on a column of silica (50% CH2Cl2 50% EtOAc)

Sources & evidence

ORD record
ord-c9c708fd712d4571bc693349129fd231
Source dataset
uspto-grants-1999_11
Patent number
US05981776

Reaction notes

Loading…