Allyltrimethylsilane → HCID 15460166, compound

HRID 483774Notes

Reaction equation

HRID 483774 reaction equation
[C:1]([O:4][C@H:5]1[CH2:10][CH2:9][C@H:8]2[C@H:11]3[C@H:21]([CH2:22][CH2:23][C@:6]12[CH3:7])[C@:19]1([CH3:20])[C:14](=[CH:15][C:16](=[O:24])[CH2:17][CH2:18]1)[CH:13]=[CH:12]3)(=[O:3])[CH3:2].[CH2:25]([Si](C)(C)C)[CH:26]=[CH2:27]>ClCCl.CCOCC.[Ti](Cl)(Cl)(Cl)Cl>[C:1]([O:4][C@H:5]1[CH2:10][CH2:9][C@H:8]2[C@H:11]3[C@H:21]([CH2:22][CH2:23][C@:6]12[CH3:7])[C@:19]1([CH3:20])[C:14](=[CH:15][C:16](=[O:24])[CH2:17][CH2:18]1)[CH2:13][C@H:12]3[CH2:27][CH:26]=[CH2:25])(=[O:3])[CH3:2]

Participants

6

Reactant 2

HCID 69808AllyltrimethylsilaneHCID 9858639HCID 9858639, compound

Product 1

HCID 15460166HCID 15460166, compound

Reagents, catalysts & solvents 3

HCID 24193Titanium TetrachlorideCatalystHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 17β-acetoxy-4,6-androstadien-3-one 1 (2.0 g, 6.1 mmol) in dry dichloromethane (130 ml) was added titanium tetrachloride (5.36 g, 3.1 ml, 28 mmol) at -70° C. The reaction mixture was allowed to stir for 5 min. Then, a solution of allyltrimethylsilane (4.0 g, 5.6 ml, 35 mmol) in dry dichloromethane (10 ml) was added over a period of 10 min and the resulting solution stirred during 1 hour at -70° C. followed by 1 hour at -20° C. Afterwards, the solution was diluted with 150 ml of ether and was washed with water (6×100 ml), dried, filtrated and concentrated to yield the crude 17β-acetoxy-7α-allyl-4-androsten-3-one which was immediately hydrolyzed.

Workup

  1. stirringthe resulting solution stirred during 1 hour at -70° C.
  2. waitfollowed by 1 hour at -20° C
  3. washwas washed with water (6×100 ml)
  4. customdried
  5. filtrationfiltrated
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ce0ba06b174b46f2b1c00b82e3a92449
Source dataset
uspto-grants-1993_07
Patent number
US05227375

Reaction notes

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