Potassium Hydroxide → HCID 11389645, compound

HRID 1716339Notes

Reaction equation

HRID 1716339 reaction equation
I[C@@H:2]1[CH2:7][CH2:6][C@H:5]2[C:8]([O:10][C@@H:3]1[CH2:4]2)=[O:9].[CH:11]1(C(O)=O)CCC=C[CH2:12]1.N12CCCN=C1CCCCC2.I.[C@H]12C(=O)[O:38][C@@H](C1)C=CC2.[OH-].[K+]>C(O)C>[OH:10][C@@H:3]1[CH2:4][C@H:5]([C:8]([O:9][CH2:11][CH3:12])=[O:38])[CH2:6][CH:7]=[CH:2]1

Participants

8

Reactant 6

HCID 14797Potassium HydroxideHCID 209033-Cyclohexene-1-carboxylic acidHCID 24841Hydrogen iodideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 1140249819914-92-2HCID 86761182HCID 86761182, compound

Product 1

HCID 11389645HCID 11389645, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The title compound was prepared, in racemic form, by generating (1R*,3R*,4R*)-4-iodocyclohexane-1,3-carbolactone from cyclohex-3-ene carboxylic acid, which was then treated with the base DBU (1,8-diazabicyclo[5.4.0]undec-7-ene) to eliminate HI. The resultant (1R*,5S*)-cyclohex-3-ene-1,5-carbolactone was then treated with potassium hydroxide dissolved in ethanol to yield the title compound (Marshall, J. A., and Shiping, X., 1995)

Workup

  1. customThe title compound was prepared, in racemic form

Sources & evidence

ORD record
ord-b99d0e9fce07440183d935fda2c906d9
Source dataset
uspto-grants-2010_09
Patent number
US07803808B2

Reaction notes

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