Tetrahydrofuran → HCID 53978241、化合物

HRID 1684565ノート

反応式

HRID 1684565 の反応式
[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]

参加物

4

反応物 3

HCID 8028TetrahydrofuranHCID 86751003HCID 86751003、化合物HCID 178506316HCID 178506316、化合物

生成物 1

HCID 53978241HCID 53978241、化合物

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-788930b7e40e45a09fef5e4d8b2a9171
出典データセット
uspto-grants-1997_06
特許番号
US05641765

反応ノート

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