Sodium Carbonate → HCID 21328862, compound

HRID 614302Notes

Reaction equation

HRID 614302 reaction equation
[OH:1][C:2]([CH3:23])([CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])/[CH:3]=[CH:4]/[CH:5]1[CH2:7][C:6]1([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:8]([O:10][CH2:11][CH3:12])=[O:9].O.[C:25]1(C)C=[CH:29][C:28](S(O)(=O)=O)=[CH:27][CH:26]=1.C([O-])([O-])=[O:37].[Na+].[Na+]>O1C=CCCC1>[O:37]1[CH2:29][CH2:28][CH2:27][CH2:26][CH:25]1[O:1][C:2]([CH3:23])([CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])/[CH:3]=[CH:4]/[CH:5]1[CH2:7][C:6]1([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:13]([O:15][CH2:16][CH3:17])=[O:14]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 21328844HCID 21328844, compound

Product 1

HCID 21328862HCID 21328862, compound

Reagents, catalysts & solvents 1

HCID 80803,4-dihydro-2H-pyranSolvent

Procedure

A solution of diethyl trans-2-(3-hydroxy-3-methyl-1-octenyl)cyclopropane-1,1-dicarboxylate (22.4 g), described in Example 31, dihydropyran (80 ml, distilled over sodium) and p-toluenesulfonic acid monohydrate (300 mg) is allowed to stand at room temperature for 30 min. After adding a few ml of 10% Na2CO3 solution the mixture is extracted with ether. The ether extract is washed with water, dried (Na2SO4) and evaporated. Purification of the residue by chromatography on silica gel gives the title compound, nmr (CDCl3) δ 0.87 (t, 3H), 2.48 (m, 1H), 4.6 (1H), 5.5 (m, 2H).

Workup

  1. extractionis extracted with ether
  2. extractionThe ether extract
  3. washis washed with water
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. customPurification of the residue by chromatography on silica gel

Sources & evidence

ORD record
ord-d0687c0d0c1b46de99699c46e7f3fe8b
Source dataset
uspto-grants-1979_03
Patent number
US04144251

Reaction notes

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