Water → HCID 13097322, compound

HRID 2198574Notes

Reaction equation

HRID 2198574 reaction equation
Cl[C:2]1[C:3]2([C:13]([CH3:15])([CH3:14])[CH:12]2[C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:4]2[C:9]([C:10]=1[Cl:11])=[CH:8][CH:7]=[CH:6][CH:5]=2.CC(C)([O-])C.[K+].O>C(O)(C)(C)C>[Cl:11][C:10]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]2([C:13]([CH3:14])([CH3:15])[CH:12]2[C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:2]=1

Participants

5

Reactant 3

HCID 962WaterHCID 23665647Potassium tert-butoxideHCID 86736987HCID 86736987, compound

Product 1

HCID 13097322HCID 13097322, compoundYield 65.7%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent2×

Procedure

A solution of 2', 3'-dichloro-3,3-dimethyl-spiro-[cyclopropane-1,1'-indene]-2-carboxylic acid-, ethyl ester (19 g as is, containing iodobenzene) in t-butanol (50 ml) is added to a 0.1 M solution of potassium-t-butoxide in t-butanol (450 ml; 0.045 mole) and the mixture allowed to stir overnight at room temperature. The reaction mixture is then poured into water, extracted with ether, the ether extracts dried over magnesium sulfate and evaporated to dryness to afford 11.1 g of a black oil. This oil is purified by chromatography (silica gel; eluent: 1:1 mixture of methylene chloride:hexane), to afford 2 g of title product, a yellow oil.

Workup

  1. extractionextracted with ether
  2. dry with materialthe ether extracts dried over magnesium sulfate
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-bc0bea2071ce402b996f2688153544a6
Source dataset
uspto-grants-1982_11
Patent number
US04358607

Reaction notes

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