Water → HCID 86734225, compound

HRID 1731139Notes

Reaction equation

HRID 1731139 reaction equation
[CH3:1][C:2]1(CO)[C:7]2[CH2:8][C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=3[C:6]=2[CH2:5][CH2:4][O:3]1.[C:17]1([CH3:27])[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=1.O>N1C=CC=CC=1>[CH3:1][CH:2]1[C:7]2[CH2:8][C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=3[C:6]=2[CH2:5][CH2:4][O:3]1.[S:23]([C:20]1[CH:21]=[CH:22][C:17]([CH3:27])=[CH:18][CH:19]=1)([O:3][CH3:2])(=[O:25])=[O:24]

Participants

5

Reactant 3

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 21495293HCID 21495293, compound

Product 1

HCID 86734225HCID 86734225, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

1-Methyl-1,3,4,9-tetrahydroindeno[2,1-c]pyran-1-methanol (9.0 g), described in Example 462, is dissolved in dry pyridine (20 ml.). p-Toluenesulfonyl chloride (7.4 g) is added portionwise to the vigorously stirred and cooled solution. The mixture is stirred further at 0° C for 1 hr., ice and water is then added and the aqueous mixture is extracted with ether. The combined ether extracts are washed with 10% ice-cold hydrochloric acid, water, 5% sodium bicarbonate water and dried (Na2SO4). Concentration of the extracts affords 1-methyl-1,3,4,9-tetrahydroindeno[2,1-c]pyran-1-methyl tosylate.

Workup

  1. temperaturecooled solution
  2. stirringThe mixture is stirred further at 0° C for 1 hr
  3. extractionthe aqueous mixture is extracted with ether
  4. washThe combined ether extracts are washed with 10% ice-cold hydrochloric acid, water, 5% sodium bicarbonate water
  5. dry with materialdried (Na2SO4)

Sources & evidence

ORD record
ord-ea2dd54465bc4d73bb0ce79828fa42a0
Source dataset
uspto-grants-1976_11
Patent number
US03995052

Reaction notes

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