Pyridine → HCID 54278690, compound

HRID 566890Notes

Reaction equation

HRID 566890 reaction equation
[OH:1][C@H:2]1[CH2:23][CH2:22][C@@:21]2([CH3:24])[C@@H:4]([CH2:5][CH2:6][C:7]3[C:8]4[C@:17]([CH3:25])([CH2:18][CH2:19][C:20]=32)[C@@H:11]([C@H:12]([CH3:16])[CH2:13][CH:14]=[O:15])[CH2:10][CH:9]=4)[C:3]1([CH3:27])[CH3:26].N1C=CC=CC=1.[C:34](Cl)(=[O:41])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>O>[C:34]([O:1][C@H:2]1[CH2:23][CH2:22][C@@:21]2([CH3:24])[C@@H:4]([CH2:5][CH2:6][C:7]3[C:8]4[C@:17]([CH3:25])([CH2:18][CH2:19][C:20]=32)[C@@H:11]([C@H:12]([CH3:16])[CH2:13][CH:14]=[O:15])[CH2:10][CH:9]=4)[C:3]1([CH3:26])[CH3:27])(=[O:41])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 7412Benzoyl chlorideHCID 54342988HCID 54342988, compound

Product 1

HCID 54278690HCID 54278690, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
4 °C

Procedure

iv)—A solution of the aldehyde (12.3 g) mentioned above in dry pyridine (150 ml) was cooled to 4° C. Benzoyl chloride (8 ml) was added in 5 min. and the reaction mixture was stirred for 1.5 h at room temperature. Then it was poured into water (2 l) and the resulting mixture was stirred overnight. The product was extracted into dichloromethane and the combined organic phases were concentrated under reduced pressure to give (3β,5α,20R)-3-(benzoyloxy)-4,4,20-trimethylpregna-8,14-diene-21-carboxaldehyde (16.1 g). The product was used in the following step without further purification.

Workup

  1. stirringthe resulting mixture was stirred overnight
  2. extractionThe product was extracted into dichloromethane
  3. concentrationthe combined organic phases were concentrated under reduced pressure

Sources & evidence

ORD record
ord-253a17a007a54d07b327bbadce7e74ee
Source dataset
uspto-grants-2001_01
Patent number
US06177420B1

Reaction notes

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