Benzene → HCID 57323924, compound

HRID 1701491Notes

Reaction equation

HRID 1701491 reaction equation
[CH3:1][O:2][C:3]([CH2:5][C@H:6]([CH3:28])[C@@H:7]1[C@:24]2([CH3:25])[C@H:10]([C@H:11]3[C@H:21]([CH2:22][CH2:23]2)[C@:19]2([CH3:20])[C:14]([CH2:15][C@@H:16]([OH:27])[CH2:17][C@@H:18]2[OH:26])=[CH:13][CH2:12]3)[CH2:9][CH2:8]1)=[O:4].[CH:29]1[CH:34]=[CH:33][CH:32]=[CH:31]C=1.C1(C)C=CC(S(O)(=O)=[O:42])=CC=1.[O:46]1[CH:51]=[CH:50][CH2:49][CH2:48][CH2:47]1>CCOCC>[CH3:1][O:2][C:3]([CH2:5][C@H:6]([CH3:28])[C@@H:7]1[C@:24]2([CH3:25])[C@H:10]([C@H:11]3[C@H:21]([CH2:22][CH2:23]2)[C@:19]2([CH3:20])[C:14]([CH2:15][C@@H:16]([O:27][CH:31]4[CH2:32][CH2:33][CH2:34][CH2:29][O:42]4)[CH2:17][C@@H:18]2[O:26][CH:51]2[CH2:50][CH2:49][CH2:48][CH2:47][O:46]2)=[CH:13][CH2:12]3)[CH2:9][CH2:8]1)=[O:4]

Participants

6

Reactant 4

HCID 241BenzeneHCID 6101p-Toluenesulfonic acidHCID 80803,4-dihydro-2H-pyranHCID 70582853HCID 70582853, compound

Product 1

HCID 57323924HCID 57323924, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 0.875 g of (20S)-1α,3β-dihydroxy-20-methyl-pregn-5-ene-21-carboxylic acid methyl ester in 40 ml. of absolute benzene was treated with 10 mg of anhydrous p-toluene-sulphonic acid and 1.5 ml. of 3,4-dihydro-2H-pyran and stored at room temperature for 24 hours. The solution was diluted with ether, washed with saturated sodium bicarbonate solution and dried over sodium sulphate. After concentration and drying in vacuo, there were obtained 1.2 g of oily (20S)-1α,3β-di(tetrahydropyranyloxy)-20-methyl-pregn-5-ene-21-carboxylic acid methyl ester; [α]D =-12° (c=0.5 in chloroform).

Workup

  1. washwashed with saturated sodium bicarbonate solution
  2. dry with materialdried over sodium sulphate
  3. concentrationAfter concentration
  4. customdrying in vacuo

Sources & evidence

ORD record
ord-d5bfc63c593b4e49991327c260ba55c1
Source dataset
uspto-grants-1980_03
Patent number
US04193921

Reaction notes

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