Pyridine → HCID 13251646, compound

HRID 1156084Notes

Reaction equation

HRID 1156084 reaction equation
[CH3:1][C:2]1([CH3:10])[C:4]([CH3:6])([CH3:5])[CH:3]1[C:7](Cl)=[O:8].[C:11]1([C:17]2[CH:25]=[CH:24][CH:23]=[C:22]3[C:18]=2[CH2:19][CH:20]([OH:26])[CH2:21]3)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.N1C=CC=CC=1>C1(C)C=CC=CC=1>[CH3:1][C:2]1([CH3:10])[C:4]([CH3:6])([CH3:5])[CH:3]1[C:7]([O:26][CH:20]1[CH2:19][C:18]2[C:22](=[CH:23][CH:24]=[CH:25][C:17]=2[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:21]1)=[O:8]

Participants

5

Reactant 3

HCID 1049PyridineHCID 110410022,2,3,3-Tetramethylcyclopropane-1-carbonyl chlorideHCID 129423884-Phenyl-2,3-dihydro-1H-inden-2-ol

Product 1

HCID 13251646HCID 13251646, compoundYield 63.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In a manner similar to Example 12A, the reaction of 1.09 g (0.007 mole) of 2,2,3,3-tetramethylcyclopropanecarbonyl chloride and 1.5 g (0.007 mole) of (+)-4-phenyl-2-indanol (EE ≥95%) in the presence of 0.7 g (0.009 mole) of pyridine and 20 ml of toluene gave 1.48 g of (+)-4-phenyl-2-indanyl 2,2,3,3-tetramethylcyclopropanecarboxylate, EE≥95%. The nmr spectrum was consistent with the proposed structure.

Sources & evidence

ORD record
ord-21371540fac44d5599d35129da4a2074
Source dataset
uspto-grants-1982_06
Patent number
US04333950

Reaction notes

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