Ammonium Chloride → HCID 70167945, compound

HRID 566887Notes

Reaction equation

HRID 566887 reaction equation
[C:1]([O:9][C@H:10]1[CH2:30][CH2:29][C@@:28]2([CH3:31])[C@@H:12]([CH2:13][CH2:14][C:15]3[C:16]4[C@:24]([CH3:32])([CH2:25][CH2:26][C:27]=32)[C@@H:19]([C@@H:20]([CH:22]=[O:23])[CH3:21])[CH2:18][CH:17]=4)[C:11]1([CH3:34])[CH3:33])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:35]1([Mg]Br)[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.[Cl-].[NH4+]>O1CCCC1>[C:1]([O:9][C@H:10]1[CH2:30][CH2:29][C@@:28]2([CH3:31])[C@@H:12]([CH2:13][CH2:14][C:15]3[C:16]4[C@:24]([CH3:32])([CH2:25][CH2:26][C:27]=32)[C@@H:19]([C@H:20]([CH3:21])[CH:22]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[OH:23])[CH2:18][CH:17]=4)[C:11]1([CH3:33])[CH3:34])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 56994186HCID 56994186, compoundHCID 178418255HCID 178418255, compound

Product 1

HCID 70167945HCID 70167945, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

ix)—A solution of the aldehyde 10 (2.0 g), obtained in the previous step, in dry tetrahydrofuran (17 ml) was added dropwise to a 1 M solution of phenylmagnesium bromide (13 ml) in tetrahydrofuran. The reaction mixture was stirred at room temperature for 3 h. A saturated aqueous solution of ammonium chloride was added and the product was extracted into ethyl acetate. The combined organic phases were washed with water, dried over sodium sulfate, and concentrated under reduced pressure to give (3β,5α,20S)-4,4,20-trimethyl-21-phenylpregna-8,14-diene-3,21-diol 3-benzoate (11) (3.0 g) which was used in the following step without further purification.

Workup

  1. extractionthe product was extracted into ethyl acetate
  2. washThe combined organic phases were washed with water
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b6a31f381fe346fdabaa01cac011d36e
Source dataset
uspto-grants-2001_01
Patent number
US06177420B1

Reaction notes

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