Diethyl Ether → HCID 15341895, compound

HRID 27331Notes

Reaction equation

HRID 27331 reaction equation
[C:1]1(C)C=[CH:5][C:4](S(Cl)(=O)=O)=[CH:3][CH:2]=1.[OH:12][C@H:13]1[CH2:18][CH2:17][C@H:16]2[C@H:19]3[C@H:29]([CH2:30][CH2:31][C@:14]12[CH3:15])[C@:27]1([CH3:28])[C:22](=[CH:23][CH2:24][CH2:25][CH2:26]1)[CH2:21][CH2:20]3.C([O:34]CC)C>>[O:34]1[CH2:5][CH2:4][CH2:3][CH2:2][CH:1]1[O:12][C@H:13]1[CH2:18][CH2:17][C@H:16]2[C@H:19]3[C@H:29]([CH2:30][CH2:31][C@:14]12[CH3:15])[C@:27]1([CH3:28])[C:22](=[CH:23][CH2:24][CH2:25][CH2:26]1)[CH2:21][CH2:20]3

Participants

4

Reactant 3

HCID 3283Diethyl EtherHCID 73974-Toluenesulfonyl chlorideHCID 1102210817beta-Hydroxy-4-androstene

Product 1

HCID 15341895HCID 15341895, compound

Procedure

To 30 ml. of dihdropyran containing 450 mg. of p-toluenesulfonyl chloride was added 6.0 g. of the product of Step B and the solution was stirred at room temperature for 1 hr. The solution was then 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 crystallized (8.5 g.), and had a m.p. of 92°-96° C.

Workup

  1. additionof dihdropyran containing 450 mg
  2. washwashed with a 20% pyridine water mixture twice
  3. dry with materialwater, then brine, and dried
  4. customevaporated
  5. customto yield a pale yellow oil which
  6. customcrystallized (8.5 g.)

Sources & evidence

ORD record
ord-0b11fb745a9d4d788003567de700ae93
Source dataset
uspto-grants-1980_09
Patent number
US04220775

Reaction notes

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