N-(Hydroxymethyl)-3,4,5,6-tetrahydrophthalimide → 2,2-Dimethyl-3-(3-cyclopropylmethoxy-3-oxo-1-propenyl) cyclopropane-carboxylic acid

HRID 1762619

Reaction equation

HRID 1762619 reaction equation
[CH3:1][C:2]1([CH3:17])[CH:4]([CH:5]=[CH:6][C:7]([O:9][CH2:10][CH:11]2[CH2:13][CH2:12]2)=[O:8])[CH:3]1[C:14]([OH:16])=[O:15].O=[C:19]1C2CCCCC=2C(=O)N1CO>>[CH3:1][C:2]1([CH3:17])[CH:4]([CH:5]=[CH:6][C:7]([O:9][CH2:10][CH:11]2[CH2:13][CH2:12]2)=[O:8])[CH:3]1[C:14]([OH:16])=[O:15].[CH3:17][C:2]1([CH3:1])[CH:4]([CH:5]=[CH:6][C:7]([O:9][CH:10]([CH3:11])[CH3:19])=[O:8])[CH:3]1[C:14]([O-:16])=[O:15]

Participants

4

Reactant 2

HCID 78597N-(Hydroxymethyl)-3,4,5,6-tetrahydrophthalimideHCID 539155962,2-Dimethyl-3-(3-cyclopropylmethoxy-3-oxo-1-propenyl) cyclopropane-carboxylic acid

Product 2

HCID 539155962,2-Dimethyl-3-(3-cyclopropylmethoxy-3-oxo-1-propenyl) cyclopropane-carboxylic acidHCID 736552712,2-Dimethyl-3-(3-isopropoxy-3-oxo-1-propenyl)-cyclopropane-carboxylate

Procedure

Using the procedure of Example 9, (1R, cis, ΔZ) 2,2-dimethyl-3-(3-isopropoxy-3-oxo-1-propenyl)-cyclopropane-carboxylic acid and (1,3,4,5,6,7-hexahydro-1,3-dioxo-2H-isoindol-2-yl)-methanol were reacted to obtain (1,3,4,5,6,7-hexahydro-1,3-dioxo-2H-isoindol-2-yl)-methyl (1R, cis, ΔZ) 2,2-dimethyl-3-(3-isopropoxy-3-oxo-1-propenyl)-cyclopropane-carboxylate with a melting point of 94° C. and a specific rotation of [α]D20 =-22.5°±2° (c=0.5% in CHCl3).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-34548629723d434c8ecf787ff70b9c02
Source dataset
uspto-grants-1989_05
Patent number
US04833163

Linked notes

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