4-Toluenesulfonyl chloride → HCID 15341895, compound

HRID 354913Notes

Reaction equation

HRID 354913 reaction equation
[O:1]1[CH:6]=[CH:5][CH2:4][CH2:3][CH2:2]1.C1(C)C=CC(S(Cl)(=O)=O)=CC=1.[OH:18][C@H:19]1[CH2:24][CH2:23][C@H:22]2[C@H:25]3[C@H:35]([CH2:36][CH2:37][C@:20]12[CH3:21])[C@:33]1([CH3:34])[C:28](=[CH:29][CH2:30][CH2:31][CH2:32]1)[CH2:27][CH2:26]3>C(OCC)C>[O:1]1[CH2:2][CH2:3][CH2:4][CH2:5][CH:6]1[O:18][C@H:19]1[CH2:24][CH2:23][C@H:22]2[C@H:25]3[C@H:35]([CH2:36][CH2:37][C@:20]12[CH3:21])[C@:33]1([CH3:34])[C:28](=[CH:29][CH2:30][CH2:31][CH2:32]1)[CH2:27][CH2:26]3

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 80803,4-dihydro-2H-pyranHCID 1102210817beta-Hydroxy-4-androstene

Product 1

HCID 15341895HCID 15341895, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To 30 ml of dihydropyran containing 450 mg of p-toluenesulfonyl chloride is added 6.0 g of the product of Step B and the solution is stirred at room temperature for 1 hour. The solution is the diluted with ethyl ether and washed with a 20% pyridine water mixture twice, and then water, then brine, and dried and evaporated to yield a pale yellow oil which crystallizes (8.5 g), and has a m.p. of 92°-96° C.

Workup

  1. washwashed with a 20% pyridine water mixture twice
  2. dry with materialwater, then brine, and dried
  3. customevaporated
  4. customto yield a pale yellow oil which
  5. customcrystallizes (8.5 g)

Sources & evidence

ORD record
ord-1ac9f7de50ab4d4ab15ad5d1b19d98c5
Source dataset
uspto-grants-1983_03
Patent number
US04377584

Reaction notes

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