Tetrahydrofuran → HCID 21484438, compound

HRID 1415323Notes

Reaction equation

HRID 1415323 reaction equation
[CH3:1][O:2][C:3]([C:5]1([CH:21]=[O:22])[C:13]2[C:8](=[CH:9][C:10]([CH:15]3[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]3)=[C:11]([Cl:14])[CH:12]=2)[CH2:7][CH2:6]1)=[O:4].[O:23]1CCCC1>[Ag]=O.O>[CH3:1][O:2][C:3]([C:5]1([C:21]([OH:23])=[O:22])[C:13]2[C:8](=[CH:9][C:10]([CH:15]3[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]3)=[C:11]([Cl:14])[CH:12]=2)[CH2:7][CH2:6]1)=[O:4]

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 54332356HCID 54332356, compound

Product 1

HCID 21484438HCID 21484438, compound

Reagents, catalysts & solvents 2

HCID 92152Silver(II) oxideCatalystHCID 962WaterSolvent

Procedure

A solution of 3.0 g of crude 1-formyl-5-cyclohexyl-6-chloro-1-indanecarboxylic acid methyl ester in 30 of tetrahydrofurane and 3 ml of water is treated with 4 equivalents of silver oxide (manufactured according to Corey et al., J. Amer. Chem. Soc., 90, 5616 (1963)) and the mixture is stirred overnight at room temperature. The reaction solution is then filtered through Celite and the filtrate is partitioned between 150 ml of methylene chloride and 100 ml of 0.1 N hydrochloric acid. The organic phase is washed with twice 150 ml of water, dried over sodium sulphate and evaporated in vacuo. Chromatography of the evaporation residue on silica gel, using benzene/ethyl acetate/glacial acetic acid, 90:30:1, as the eluting agent, yields crude 1-methoxycarbonyl-5-cyclohexyl-6-chloro-1-indanecarboxylic acid which can be purified further by fractional crystallisation from benzene-hexane; melting point 139°-142° C.

Workup

  1. filtrationThe reaction solution is then filtered through Celite
  2. customthe filtrate is partitioned between 150 ml of methylene chloride and 100 ml of 0.1 N hydrochloric acid
  3. washThe organic phase is washed with twice 150 ml of water
  4. dry with materialdried over sodium sulphate
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-e046d514364f4df08b2541577969ecf3
Source dataset
uspto-grants-1977_01
Patent number
US04004026

Reaction notes

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