Diethyl Ether → HCID 70478952, compound

HRID 637617Notes

Reaction equation

HRID 637617 reaction equation
[F:1][CH:2]([F:22])[C@H:3]1[CH2:20][C@@:18]2([CH3:19])[C@@H:14]([CH2:15][CH2:16][C:17]2=[O:21])[C@H:13]2[C@H:4]1[C@@H:5]1[C:10]([CH2:11][CH2:12]2)=[CH:9][CH2:8][CH2:7][CH2:6]1.C(OCC)C.[Cl-].[NH4+].[C:30]([Mg]Br)#[C:31][CH3:32]>C1COCC1>[F:1][CH:2]([F:22])[C@H:3]1[CH2:20][C@@:18]2([CH3:19])[C@@H:14]([CH2:15][CH2:16][C@@:17]2([OH:21])[C:30]#[C:31][CH3:32])[C@H:13]2[C@H:4]1[C@@H:5]1[C:10]([CH2:11][CH2:12]2)=[CH:9][CH2:8][CH2:7][CH2:6]1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 25517Ammonium ChlorideHCID 54387093HCID 54387093, compoundHCID 178419101HCID 178419101, compound

Product 1

HCID 70478952HCID 70478952, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 11β-difluoromethylestr-4-en-17-one (XII, Example 14, 0.9 g) in propynyl magnesium bromide (0.5M, 10 ml) and THF is kept at 20°-25° for 16 hours. Diethyl ether and aqueous ammonium chloride are added and the diethyl ether phase is separated and washed with water and concentrated to a solid. The solid is purified by chromatography through silica gel using ethyl acetate/hexane (20/80) as the irrigant. The appropriate fractions are pooled and concentrated to give the title compound, IR (mull) 3400, 2237 and 1666 cm-1 ; MS (m/e) 348, 330, 315, 266 and 251; NMR (CDCl3) 0.87, 1.86 and 6.0 δ.

Workup

  1. customthe diethyl ether phase is separated
  2. washwashed with water
  3. concentrationconcentrated to a solid
  4. customThe solid is purified by chromatography through silica gel
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-ced9d80e9177442fbccd0df1c370fd13
Source dataset
uspto-grants-1985_12
Patent number
US04557867

Reaction notes

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