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Water → 20-(5,5-Dimethyl-1,3-dioxan-2-yl)pregna-1,4,6-trien-3-one

HRID 1196310
Notes
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Reaction equation

HRID 1196310 reaction equation
O[C@@H:2]1[CH2:22][C:21]2[C@:16]([CH3:24])([CH:17]=[CH:18][C:19](=[O:23])[CH:20]=2)[C@@H:15]2[C@@H:3]1[C@H:4]1[C@:12]([CH3:25])([CH2:13][CH2:14]2)[C@@H:7]([CH:8]([CH:10]=O)[CH3:9])[CH2:6][CH2:5]1.[CH3:26][C:27]([CH3:32])([CH2:30][OH:31])[CH2:28][OH:29].O>C1C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH3:26][C:27]1([CH3:32])[CH2:30][O:31][CH:10]([CH:8]([C@@H:7]2[C@:12]3([CH3:25])[C@H:4]([C@H:3]4[C@H:15]([CH2:14][CH2:13]3)[C@:16]3([CH3:24])[C:21](=[CH:20][C:19](=[O:23])[CH:18]=[CH:17]3)[CH:22]=[CH:2]4)[CH2:5][CH2:6]2)[CH3:9])[O:29][CH2:28]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 962WaterHCID 31344Neopentyl glycolHCID 228438847-Hydroxy-pregna-1,4-dien-3-one-20-carbaldehyde

Product 1

HCID 2284393220-(5,5-Dimethyl-1,3-dioxan-2-yl)pregna-1,4,6-trien-3-oneYield 92.2%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalyst
HCID 241
Benzene
Solvent

Procedure

In 200 ml of benzene were dissolved 5.00 g (14.6 mmoles) of 7α-hydroxypregna-1,4-dien-3-one-20-carbaldehyde and 4.56 g (43.8 mmoles) of 2,2-dimethyl-1,3-propanediol, followed by addition of 100 mg of p-toluenesulfonic acid. The mixture was refluxed for 5 hours, with the byproduct water being constantly removed from the reaction system by means of a Dean-Stark trap. The reaction mixture was cooled to room temperature and washed with aqueous sodium hydrogen carbonate solution. The aqueous layer was extracted with ether-hexane (70:30, v/v) and the extract was combined with the organic layer. This mixture was washed with aqueous sodium chloride solution and dried over magnesium sulfate and the solvent was distilled off under reduced pressure. Finally the residue was purified by silica gel chromatography (eleuent: ethyl acetate-hexane=1:10, v/v) to recover 5.53 g of 20-(5,5-dimethyl-1,3-dioxan-2-yl)pregna-1,4,6-trien-3-one (yield: 92%).

Workup

  1. customconstantly removed from the reaction system by means of a Dean-Stark trap
  2. washwashed with aqueous sodium hydrogen carbonate solution
  3. extractionThe aqueous layer was extracted with ether-hexane (70:30, v/v)
  4. washThis mixture was washed with aqueous sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customFinally the residue was purified by silica gel chromatography (eleuent: ethyl acetate-hexane=1:10

Sources & evidence

ORD record
ord-c728d427ec1e4e89bff843011abed7f2
Source dataset
uspto-grants-1992_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05112998

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes