Dichloromethane → HCID 13578829, compound

HRID 1285314Notes

Reaction equation

HRID 1285314 reaction equation
C1(S([CH2:9][C:10]2[CH2:29][C@@H:28]3[C@:15]([CH3:32])([CH2:16][CH:17]=[C:18]4[C@H:27]3[CH2:26][CH2:25][C:24]3[C@:19]4([CH3:31])[CH2:20][CH2:21][C:22](=[O:30])[CH:23]=3)[C:11]=2[C:12](=[O:14])[CH3:13])=O)C=CC=CC=1.C[O:34]P(OC)OC.C(Cl)Cl>C1(C)C=CC=CC=1.CO>[OH:34][C@:11]1([C@:15]2([CH3:32])[C@H:28]([C@H:27]3[C:18](=[CH:17][CH2:16]2)[C@:19]2([CH3:31])[C:24](=[CH:23][C:22](=[O:30])[CH2:21][CH2:20]2)[CH2:25][CH2:26]3)[CH2:29][C:10]1=[CH2:9])[C:12](=[O:14])[CH3:13]

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 8472Trimethyl phosphiteHCID 13578831HCID 13578831, compound

Product 1

HCID 13578829HCID 13578829, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent

Procedure

A mixture of 16-(phenylsulfinylmethyl)pregn-4,9(11),16-triene-3,20-dione (VIA, Example 14, 100 mg) in toluene (1 ml) and methanol (0.14 ml) containing 53 μl of trimethylphosphite was heated for 16 hrs at 65° in a sealed vial. TLC showed the reaction to be complete. Methylene chloride was added, the reaction mixture washed with water, the organic phase separated, dried and concentrated under reduced pressure to give the title compound. NMR (CDCl3) 0.77, 1.35, 2.31, 5.10, 5.27, 5.57 and 5.75 δ.

Workup

  1. temperaturewas heated for 16 hrs at 65° in a sealed vial
  2. customthe reaction
  3. washthe reaction mixture washed with water
  4. customthe organic phase separated
  5. customdried
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8477ce876d8347699d119ac0ff733bd5
Source dataset
uspto-grants-1986_01
Patent number
US04567001

Reaction notes

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