Methanol → [5-(3,5,5,8,8-Pentamethyl-2,3,5,6,7,8-hexahydronaphtho[2,3-b]furan-3-yl)thiophene-3-yl]carboxylic acid

HRID 1075628Notes

Reaction equation

HRID 1075628 reaction equation
[CH3:1][C:2]1([C:19]2[S:23][CH:22]=[C:21]([C:24]([O:26]C)=[O:25])[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-].[Li+].CO.O>C1COCC1>[CH3:1][C:2]1([C:19]2[S:23][CH:22]=[C:21]([C:24]([OH:26])=[O:25])[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]([CH3:15])([CH3:16])[CH2:11][CH2:10][C:9]3([CH3:17])[CH3:18]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 3939Lithium HydroxideHCID 67581120Methyl [5-(3,5,5,8,8-pentamethyl-2,3,5,6,7,8-hexahydronaphtho[2,3-b]furan-3-yl)-thiophene-3-yl]carboxylate

Product 1

HCID 70195550[5-(3,5,5,8,8-Pentamethyl-2,3,5,6,7,8-hexahydronaphtho[2,3-b]furan-3-yl)thiophene-3-yl]carboxylic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methyl [5-(3,5,5,8,8-pentamethyl-2,3,5,6,7,8-hexahydronaphtho[2,3-b]furan-3-yl)-thiophene-3-yl]carboxylate (2.1 g, 5.4 mmol), lithium hydroxide (2g, 48 mmol), methanol (1 ml) and water (1 ml) in 30 ml of THF was heated under reflux for 6 h. After concentrating in a rotary evaporator under vacuum at 40° C., adding water, ethyl ether and acidifying with a concentrated hydrochloric acid solution to pH 1, the organic phase was washed twice with water, dried over magnesium sulfate and concentrated in a rotary evaporator under vacuum at 40° C. The solids obtained were washed with heptane.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 6 h
  3. concentrationAfter concentrating in a rotary evaporator under vacuum at 40° C.
  4. additionadding water, ethyl ether and acidifying with a concentrated hydrochloric acid solution to pH 1
  5. washthe organic phase was washed twice with water
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated in a rotary evaporator under vacuum at 40° C
  8. customThe solids obtained
  9. washwere washed with heptane

Sources & evidence

ORD record
ord-3fea9b24387c44dd8e791f645142e034
Source dataset
uspto-grants-1999_05
Patent number
US05905088

Reaction notes

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