Hydrochloric Acid → (1RS,2SR,6RS,7RS)-8-ethynyl-4-(2,4,6-trimethylphenyl)-10-oxatricyclo-[5.2.1.02,6]decane-3,5-dione

HRID 407848Notes

Reaction equation

HRID 407848 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH3:7][C:8]1[CH:13]=[C:12]([CH3:14])[CH:11]=[C:10]([CH3:15])[C:9]=1[CH:16]1[C:24](=[O:25])[CH:23]2[CH:18]([CH:19]3[O:26][CH:22]2[CH:21]([C:27]#[C:28][Si](C)(C)C)[CH2:20]3)[C:17]1=[O:33].Cl>CO>[C:27]([CH:21]1[CH2:20][CH:19]2[O:26][CH:22]1[CH:23]1[CH:18]2[C:17](=[O:33])[CH:16]([C:9]2[C:10]([CH3:15])=[CH:11][C:12]([CH3:14])=[CH:13][C:8]=2[CH3:7])[C:24]1=[O:25])#[CH:28]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 67283755(1RS,2SR,6RS,7RS)-4-(2,4,6-trimethylphenyl)-8-trimethylsilylethynyl-10-oxatricyclo-[5.2.1.02,6]decane-3,5-dione

Product 1

HCID 86664120(1RS,2SR,6RS,7RS)-8-ethynyl-4-(2,4,6-trimethylphenyl)-10-oxatricyclo-[5.2.1.02,6]decane-3,5-dione

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Potassium carbonate (2.58 g, 19 mmol) is added to a stirred solution of (1RS,2SR,6RS,7RS)-4-(2,4,6-trimethylphenyl)-8-trimethylsilylethynyl-10-oxatricyclo-[5.2.1.02,6]decane-3,5-dione (6.43 g, 17 mmol) in methanol (100 ml). The reaction mixture is stirred at room temperature for 2 hours and 30 minutes, then dilute aqueous hydrochloric acid is added and the mixture is extracted with ethyl acetate. The organic extracts are combined, dried over anhydrous magnesium sulfate, filtered and the filtrate is evaporated under reduced pressure to give (1RS,2SR,6RS,7RS)-8-ethynyl-4-(2,4,6-trimethylphenyl)-10-oxatricyclo-[5.2.1.02,6]decane-3,5-dione.

Workup

  1. extractionthe mixture is extracted with ethyl acetate
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. customthe filtrate is evaporated under reduced pressure

Sources & evidence

ORD record
ord-0f8f72879ef74446ba3a4ca37af2e1a0
Source dataset
uspto-grants-2014_06
Patent number
US08754242B2

Reaction notes

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