3-Furanmethanol, 5-(phenylmethyl)- → 2,2-Dimethyl-3-(3-cyclobutoxy-3-oxo-1-propenyl)-cyclopropane-carboxylic acid

HRID 1762616Notes

Reaction equation

HRID 1762616 reaction equation
[CH3:1][C:2]1([CH3:17])[CH:4]([CH:5]=[CH:6][C:7]([O:9][CH:10]2[CH2:13][CH2:12][CH2:11]2)=[O:8])[CH:3]1[C:14]([OH:16])=[O:15].C(C1OC=C(CO)C=1)C1C=CC=CC=1>C(Cl)(Cl)Cl>[CH3:1][C:2]1([CH3:17])[CH:4]([CH:5]=[CH:6][C:7]([O:9][CH:10]2[CH2:11][CH2:12][CH2:13]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]([CH3:13])[CH3:11])=[O:8])[CH:3]1[C:14]([O-:16])=[O:15]

Participants

5

Reactant 2

HCID 123643963-Furanmethanol, 5-(phenylmethyl)-HCID 539623272,2-Dimethyl-3-(3-cyclobutoxy-3-oxo-1-propenyl)-cyclopropane-carboxylic acid

Product 2

HCID 539623272,2-Dimethyl-3-(3-cyclobutoxy-3-oxo-1-propenyl)-cyclopropane-carboxylic acidHCID 736552712,2-Dimethyl-3-(3-isopropoxy-3-oxo-1-propenyl)-cyclopropane-carboxylate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Using the procedure of Example 9, (1R, cis, ΔZ) 2,2-dimethyl-3-(3-isopropoxy-3-oxo-1-propenyl)-cyclopropane-carboxylic acid and 5-benzyl-3-furyl-methanol was reacted to obtain 5-benzyl-3-furyl-methyl (1R, cis, ΔZ) 2,2-dimethyl-3-(3-isopropoxy-3-oxo-1-propenyl)-cyclopropane-carboxylate with a specific rotation of [α]D20 =+44°±2° (c=0.4% in chloroform).

Workup

  1. customwas reacted

Sources & evidence

ORD record
ord-85545664228b48e6b39a5707c46be802
Source dataset
uspto-grants-1989_05
Patent number
US04833163

Reaction notes

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