Sodium Acetate → HCID 12801522, compound

HRID 2166862Notes

Reaction equation

HRID 2166862 reaction equation
[CH3:1][CH2:2][C@:3]12[CH2:19][CH2:18][C@H:17]3[C@@H:8]([CH2:9][CH2:10][C:11]4[C@@H:16]3[CH2:15][CH2:14][CH2:13][CH:12]=4)[C@@H:7]1[C@@H:6]([O:20][CH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][O:22]1)[CH2:5][C@@H:4]2[OH:27].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.C([O-])(=O)C.[Na+]>C(Cl)Cl>[CH3:1][CH2:2][C@:3]12[CH2:19][CH2:18][C@H:17]3[C@@H:8]([CH2:9][CH2:10][C:11]4[C@@H:16]3[CH2:15][CH2:14][CH2:13][CH:12]=4)[C@@H:7]1[C@@H:6]([O:20][CH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][O:22]1)[CH2:5][C:4]2=[O:27]

Participants

5

Reactant 3

HCID 517045Sodium AcetateHCID 12801520HCID 12801520, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 12801522HCID 12801522, compoundYield 61.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

At 0° C., 2.6 g of 18-methyl-15α-tetrahydropyran-2-yloxy-4-estren-17β-ol in 50 ml of methylene chloride is stirred with 3.6 g of pyridinium chlorochromate and 1.2 g of sodium acetate at 0° C. After 3.5 hours, the mixture is diluted with methylene chloride, washed with water, and dried. Chromatography of the crude product on silica gel with 3-3.5% acetone/hexane yields 1.6 g of 18-methyl-15α-tetrahydropyran-2-yloxy-4-estren-17-one as an oil. [α]D20 =+87.4°.

Workup

  1. washwashed with water
  2. customdried

Sources & evidence

ORD record
ord-efce03cef93c4d8bb3f905d9be4c1cf9
Source dataset
uspto-grants-1983_06
Patent number
US04390530

Reaction notes

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