Water → 3-Ethynyl-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthaldehyde

HRID 1836879Notes

Reaction equation

HRID 1836879 reaction equation
C[Si](C)(C)[C:3]#[C:4][C:5]1[C:6]([CH:19]=[O:20])=[CH:7][C:8]2[C:9]([CH3:18])([CH3:17])[CH2:10][CH2:11][C:12]([CH3:16])([CH3:15])[C:13]=2[CH:14]=1.C(=O)([O-])[O-].[K+].[K+].O>CO>[C:4]([C:5]1[C:6]([CH:19]=[O:20])=[CH:7][C:8]2[C:9]([CH3:18])([CH3:17])[CH2:10][CH2:11][C:12]([CH3:15])([CH3:16])[C:13]=2[CH:14]=1)#[CH:3]

Participants

5

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 23498929HCID 23498929, compound

Product 1

HCID 234989213-Ethynyl-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthaldehydeYield 73%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 7.21 g (23.1 mmol) of 3-(2-trimethylsilyl-ethynyl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthaldehyde in 150 mL of methanol was added 6.38 g (46.2 mmol) of potassium carbonate. After 1 hour, the reaction mixture was poured into water and extracted with ethyl acetate. The organic phase was washed with brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The product was purified by flash chromatography on silica gel (3% ethyl acetate/hexane) to afford 4.04 g (73%) of 3-ethynyl-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthaldehyde (m.p.=94.0-94.6° C.).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic phase was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe product was purified by flash chromatography on silica gel (3% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-b8cbcb18fac2423289b1345f35752dd3
Source dataset
uspto-grants-2004_08
Patent number
US06777418B2

Reaction notes

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