2-(1,3-Dioxolan-2-yl)-3-[1-hydroxy-1-(thiophene-2-yl)methyl]-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene → 2-Formyl-3-[(thiophene-2-yl)methyl]-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene

HRID 1836889Notes

Reaction equation

HRID 1836889 reaction equation
[O:1]1CCO[CH:2]1[C:6]1[C:15]([CH:16](O)[C:17]2[S:18][CH:19]=[CH:20][CH:21]=2)=[CH:14][C:13]2[C:12]([CH3:24])([CH3:23])[CH2:11][CH2:10][C:9]([CH3:26])([CH3:25])[C:8]=2[CH:7]=1>C(OCC)(=O)C.[Pd]>[CH:2]([C:6]1[C:15]([CH2:16][C:17]2[S:18][CH:19]=[CH:20][CH:21]=2)=[CH:14][C:13]2[C:12]([CH3:24])([CH3:23])[CH2:11][CH2:10][C:9]([CH3:26])([CH3:25])[C:8]=2[CH:7]=1)=[O:1]

Participants

4

Reactant 1

HCID 234989602-(1,3-Dioxolan-2-yl)-3-[1-hydroxy-1-(thiophene-2-yl)methyl]-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene

Product 1

HCID 234989152-Formyl-3-[(thiophene-2-yl)methyl]-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthaleneYield 62%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

The alcohol prepared above was dissolved in 7 mL of ethyl acetate and 75 mg of 10% Pd/C was added and the reaction mixture stirred under a hydrogen atmosphere for about 4 hours. The reaction mixture was filtered through Celite and concentrated in vacuo. The resulting residue was purified by preparative thin layer chromatography (10% ethyl acetate/hexane) to give 2-formyl-3-[(thiophene-2-yl)methyl]-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene (94 mg, 62%) directly.

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. concentrationconcentrated in vacuo
  3. customThe resulting residue was purified by preparative thin layer chromatography (10% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-0b4238cb6de846cab46470d87d26fd41
Source dataset
uspto-grants-2004_08
Patent number
US06777418B2

Reaction notes

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