Water → HCID 13714533, compound

HRID 434190Notes

Reaction equation

HRID 434190 reaction equation
O.C1O[CH:5]([C:6]2[CH:11]=[CH:10][C:9]([C@H:12]3[CH2:29][C@@:27]4([CH3:28])[C@@H:23]([CH2:24][CH2:25][C@:26]4([C:32]#[CH:33])[O:30]C)[C@H:22]4[C:13]3=[C:14]3[C@@:19](O)([CH2:20][CH2:21]4)[CH2:18][C:17](OC)([O:35]C)[CH2:16][CH2:15]3)=[CH:8][CH:7]=2)[O:4]C1.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)(O)[O-].[Na+]>CC(C)=O>[C:32]([C@:26]1([OH:30])[CH2:25][CH2:24][C@H:23]2[C@H:22]3[C:13]([C@@H:12]([C:9]4[CH:10]=[CH:11][C:6]([CH:5]=[O:4])=[CH:7][CH:8]=4)[CH2:29][C@:27]12[CH3:28])=[C:14]1[C:19](=[CH:18][C:17](=[O:35])[CH2:16][CH2:15]1)[CH2:20][CH2:21]3)#[CH:33]

Participants

6

Reactant 4

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 516892Sodium BicarbonateHCID 12044130HCID 12044130, compound

Product 1

HCID 13714533HCID 13714533, compoundYield 46.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Water (2 ml) is added to 1.2 g of 4-(3,3-dimethoxy-17α-ethinyl-5α-hydroxy-17β-methoxy-estr-9-en-11β-yl)benzaldehyde ethylene acetal in 20 ml of acetone. After the addition of 300 mg of 4-toluenesulfonic acid, the mixture is stirred for 2 hours at room temperature. The reaction solution is stirred into 300 ml of ice water, a flaky precipitate being obtained. After neutralization with sodium bicarbonate solution and stirring for 30 minutes, the precipitate is filtered off with suction, washed with water and dried under vacuum, 786 mg being obtained as a yellow foam. The crude product is purified by preparative layer chromatography on silica gel PF254+366nm (MERCK AG) with a mixture of 4:1 of toluene:acetone as mobile phase, 430 mg of 4-(17α-ethinyl-17β-hydroxy-3-oxoestra-4,9-diene-11β-yl)benzaldehyde being obtained. The product is recrystallized from boiling t-butyl methyl ether with addition of n-hexane.

Workup

  1. customa flaky precipitate being obtained
  2. filtrationthe precipitate is filtered off with suction
  3. washwashed with water
  4. customdried under vacuum, 786 mg
  5. custombeing obtained as a yellow foam
  6. customThe crude product is purified by preparative layer chromatography on silica gel PF254+366nm (MERCK AG) with a mixture of 4:1 of toluene

Sources & evidence

ORD record
ord-414d555d2ac646a2b6034bb67d555f52
Source dataset
uspto-grants-2003_12
Patent number
US06670493B2

Reaction notes

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