Tetrahydrofuran → HCID 19900606, compound

HRID 1029990Notes

Reaction equation

HRID 1029990 reaction equation
[C:1](=[O:48])([O:17][C:18]1[C:19]([CH3:47])=[C:20]2[C:25](=[C:26]([CH3:29])[C:27]=1[CH3:28])[O:24][C:23]([CH3:46])([CH2:30][CH2:31][CH2:32][CH:33]([CH3:45])[CH2:34][CH2:35][CH2:36][CH:37]([CH3:44])[CH2:38][CH2:39][CH2:40][CH:41]([CH3:43])[CH3:42])[CH2:22][CH2:21]2)[O:2][CH2:3][C:4]1([CH3:16])[O:15][CH:5]1[CH2:6][O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[O:49]1CCCC1.Cl(O)(=O)(=O)=O>O>[C:1](=[O:48])([O:17][C:18]1[C:19]([CH3:47])=[C:20]2[C:25](=[C:26]([CH3:29])[C:27]=1[CH3:28])[O:24][C:23]([CH3:46])([CH2:30][CH2:31][CH2:32][CH:33]([CH3:45])[CH2:34][CH2:35][CH2:36][CH:37]([CH3:44])[CH2:38][CH2:39][CH2:40][CH:41]([CH3:42])[CH3:43])[CH2:22][CH2:21]2)[O:2][CH2:3][C:4]([OH:49])([CH3:16])[CH:5]([OH:15])[CH2:6][O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 24247Perchloric AcidHCID 19900638HCID 19900638, compound

Product 1

HCID 19900606HCID 19900606, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

8.6 g (0.013 mol) of 4-benzyloxy-2,3-epoxy-2-methylbutyl 2,5,7,8-tetramethyl-2-(4',8',12'-trimethyltridecyl)-6-chromanyl carbonate, 150 ml of tetrahydrofuran and 30 ml of water were mixed together. To the obtained mixture was slowly added dropwise a solution of 7 ml of 60% perchloric acid in 20 ml of water under ice-cooling and stirring. After the completion of the addition, the mixture was further stirred at the same temperature for 4 hours and then poured into water. After confirming that no peroxide remained therein with potassium iodide starch paper, the mixture was extracted with ether. The extract was washed with water and dried. After distilling off the solvent, the obtained oily residue was purified by column chromatography (silica gel, benzene:ethyl acetate=8:2). Thus 4.8 g of the title compound was obtained as a pale yellow, viscous liquid.

Workup

  1. temperaturecooling
  2. additionAfter the completion of the addition
  3. stirringthe mixture was further stirred at the same temperature for 4 hours
  4. extractionwith potassium iodide starch paper, the mixture was extracted with ether
  5. washThe extract was washed with water
  6. customdried
  7. distillationAfter distilling off the solvent
  8. customthe obtained oily residue was purified by column chromatography (silica gel, benzene:ethyl acetate=8:2)

Sources & evidence

ORD record
ord-e55abdbf59454afb83482932a715aa80
Source dataset
uspto-grants-1992_04
Patent number
US05102895

Reaction notes

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