Tetrahydrofuran → HCID 53978241, compound

HRID 1684565Notes

Reaction equation

HRID 1684565 reaction equation
[F:1][C:2]([F:9])([F:8])[CH2:3][CH2:4][CH2:5][Mg]Br.[CH3:10][C@:11]12[CH2:28][CH2:27][C@H:26]3[C@@H:16]([CH2:17][CH:18]=[C:19]4[C@:24]3([CH3:25])[CH2:23][CH2:22][C:21]([CH2:29][OH:30])=[CH:20]4)[C@@H:15]1[CH2:14][CH2:13][CH2:12]2.C1C[O:34][CH2:33]C1>>[F:1][C:2]([F:9])([F:8])[CH2:3][CH2:4][CH2:5][CH:33]([C@H:12]1[CH2:13][CH2:14][C@H:15]2[C@H:16]3[C@H:26]([CH2:27][CH2:28][C@:11]12[CH3:10])[C@:24]1([CH3:25])[C:19]([CH:20]=[C:21]([CH2:29][OH:30])[CH2:22][CH2:23]1)=[CH:18][CH2:17]3)[OH:34]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 86751003HCID 86751003, compoundHCID 178506316HCID 178506316, compound

Product 1

HCID 53978241HCID 53978241, compound

Procedure

4,4,4-trifluorobutyl magnesium bromide (0.25M in THF, 4.0 ml, 1.0 mmol) was added to a solution of (17β)-17-carboxaldehydo- androsta-3,5-diene-3-methanol (50 mg, 0.16 mmol) in THF at 0 degrees C. After 0.5 h the reaction was quenched with aqueous ammonium chloride, the aqueous layer was extracted with EtOAc, the combined organic extracts were dried (MgSO4), filtered, concentrated, and chromatographed (silica gel, 20% EtOAc) to yield the title compound.

Workup

  1. customAfter 0.5 h the reaction was quenched with aqueous ammonium chloride
  2. extractionthe aqueous layer was extracted with EtOAc
  3. dry with materialthe combined organic extracts were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customchromatographed (silica gel, 20% EtOAc)

Sources & evidence

ORD record
ord-788930b7e40e45a09fef5e4d8b2a9171
Source dataset
uspto-grants-1997_06
Patent number
US05641765

Reaction notes

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