Lithium Hydroxide → HCID 9799185, compound

HRID 1075623Notes

Reaction equation

HRID 1075623 reaction equation
[CH3:1][C:2]1([C:19]2[CH:29]=[CH:28][C:22]([C:23]([O:25]CC)=[O:24])=[CH:21][CH:20]=2)[CH2:6][O:5][C:4]2[CH:7]=[C:8]3[C:13](=[CH:14][C:3]1=2)[C:12]([CH3:16])([CH3:15])[CH2:11][CH2:10][C:9]3([CH3:18])[CH3:17].[OH-].[Na+].[OH-].[Li+].C1COCC1>O.CO>[CH3:1][C:2]1([C:19]2[CH:20]=[CH:21][C:22]([C:23]([OH:25])=[O:24])=[CH:28][CH:29]=2)[CH2:6][O:5][C:4]2[CH:7]=[C:8]3[C:13](=[CH:14][C:3]1=2)[C:12]([CH3:15])([CH3:16])[CH2:11][CH2:10][C:9]3([CH3:17])[CH3:18]

Participants

7

Reactant 4

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 70193470HCID 70193470, compound

Product 1

HCID 9799185HCID 9799185, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of ethyl (-)-4-(3,5,5,8,8-pentamethyl-2,3,5,6,7,8-hexahydronaphtho[2,3-b]furan-3-yl)benzoate (200 mg, 0.5 mmol), sodium hydroxide (100 mg, 2.4 mmol), and lithium hydroxide (100 mg, 2.4 mmol) in 5 ml of a solution of THF, methanol and water (5/1/1) was heated under reflux for 24 h. The reaction medium was concentrated in a rotary evaporator under vacuum at 40° C. After adding 5 ml of water and 5 ml of ethyl ether and acidifying with a concentrated hydrochloric acid solution to pH 1, the organic phase was washed twice with 5 ml of water, dried over magnesium sulfate and concentrated in a rotary evaporator under vacuum at 40° C. The solid obtained was washed with heptane.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 24 h
  3. concentrationThe reaction medium was concentrated in a rotary evaporator under vacuum at 40° C
  4. additionAfter adding 5 ml of water and 5 ml of ethyl ether and acidifying with a concentrated hydrochloric acid solution to pH 1
  5. washthe organic phase was washed twice with 5 ml of water
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated in a rotary evaporator under vacuum at 40° C
  8. customThe solid obtained
  9. washwas washed with heptane

Sources & evidence

ORD record
ord-d35258c123cb415d9981e0f09a4bc4a8
Source dataset
uspto-grants-1999_05
Patent number
US05905088

Reaction notes

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