Water → HCID 59591529, compound

HRID 1942580Notes

Reaction equation

HRID 1942580 reaction equation
C[Si](C)(C)[O:3][C:4](=[CH2:18])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17].[O:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH:22]1[O:27][C:28]1[CH:33]=[CH:32][C:31]([CH2:34][CH2:35][C:36](=[O:61])[C:37]#[C:38][CH2:39][C:40]2([CH2:46][CH2:47][C:48]3[CH:53]=[CH:52][C:51]([O:54][CH:55]4[CH2:60][CH2:59][CH2:58][CH2:57][O:56]4)=[CH:50][CH:49]=3)[S:45][CH2:44][CH2:43][CH2:42][S:41]2)=[CH:30][CH:29]=1.O.C(OCC)(=O)C>C1COCC1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>[O:56]1[CH2:57][CH2:58][CH2:59][CH2:60][CH:55]1[O:54][C:51]1[CH:52]=[CH:53][C:48]([CH2:47][CH2:46][C:40]2([CH2:39][CH:38]([CH2:18][C:4](=[O:3])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH2:37][C:36](=[O:61])[CH2:35][CH2:34][C:31]3[CH:32]=[CH:33][C:28]([O:27][CH:22]4[CH2:23][CH2:24][CH2:25][CH2:26][O:21]4)=[CH:29][CH:30]=3)[S:41][CH2:42][CH2:43][CH2:44][S:45]2)=[CH:49][CH:50]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 11483399HCID 11483399, compoundHCID 131730271HCID 131730271, compound

Product 1

HCID 59591529HCID 59591529, compound

Reagents, catalysts & solvents 2

HCID 2724141Tetrabutylammonium FluorideCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

Trimethyl-(1-methylene-tetradecyloxy)-silane (176 mg, 0.6 mmol) and the enone 21 (176 mg, 0.3 mmol) are dissolved in 2 mL of anhydrous THF and the solution is cooled down to −78° C. Two drops of tetrabutylammonium fluoride (1 M in THF) are injected. The mixture is stirred for 1 h at this temperature, then the solution is left to return to ambient temperature under stirring. After the addition of water and extraction with ethyl acetate, the product is dried and the solvent is evaporated off. The residue is purified by flash chromatography in order to produce compound 22.

Workup

  1. waitthe solution is left
  2. customto return to ambient temperature
  3. stirringunder stirring
  4. customthe product is dried
  5. customthe solvent is evaporated off
  6. customThe residue is purified by flash chromatography in order

Sources & evidence

ORD record
ord-86990b82f7f84fa2a267d2956957a678
Source dataset
uspto-grants-2013_03
Patent number
US08389569B2

Reaction notes

Loading…