Sulfuric Acid → HCID 131718633, compound

HRID 1741974Notes

Reaction equation

HRID 1741974 reaction equation
[Si:1]([O:8][CH2:9][CH:10]1[CH:15]2[O:16][C:17]([CH3:20])([CH3:19])[O:18][CH:14]2[CH:13]([O:21][CH:22]([O:24][CH2:25][CH3:26])[CH3:23])[CH2:12][C:11]1=[CH:27][C:28](OCC)=O)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[H-].C([Al+]CC(C)C)C(C)C.S(=O)(=O)(O)[OH:44]>C1(C)C=CC=CC=1>[Si:1]([O:8][CH2:9][CH:10]1[CH:15]2[O:16][C:17]([CH3:20])([CH3:19])[O:18][CH:14]2[CH:13]([O:21][CH:22]([O:24][CH2:25][CH3:26])[CH3:23])[CH2:12][C:11]1=[C:27]([OH:44])[CH3:28])([C:4]([CH3:6])([CH3:7])[CH3:5])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 21225700DiisobutylaluminumhydrideHCID 53659819HCID 53659819, compound

Product 1

HCID 131718633HCID 131718633, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Two grams of ethyl (2-(tert-butyldimethylsilyloxymethyl)-3,4-(dimethylmethylenedioxy)-5-(1-ethoxyethoxy) cyclohexylidene)acetate were dissolved in 10 ml of dry toluene, and 4.7 ml of diisobutyl aluminum hydride (2N hexane solution, 9.4 mmol) was added at -78° C., followed by stirring the mixture for 3 hours. After stirring at 0° C. for 5 minutes, a 10% sulfuric acid aqueous solution was added gradually until the reaction mixture became white. The reaction mixture was extracted with diethyl ether. The extract was washed with a sodium hydrogen carbonate aqueous solution and a saturated sodium chloride aqueous solution in sequence. The organic layer was dried over anhydrous magnesium sulfate, and concentration was effected under reduced pressure. The obtained residue was purified by silica gel column chromatography to give 1.47 g of (2-(tert-butyldimethylsilyloxymethyl)-3,4-(dimethylmethylenedioxy)-5-(1-ethoxyethoxy)cyclohexylidene) ethanol having the following properties.

Workup

  1. stirringAfter stirring at 0° C. for 5 minutes
  2. extractionThe reaction mixture was extracted with diethyl ether
  3. washThe extract was washed with a sodium hydrogen carbonate aqueous solution
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate, and concentration
  5. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-ec5e74e12865480d8a1fe917446bb44a
Source dataset
uspto-grants-1994_08
Patent number
US05334740

Reaction notes

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