Cyclopropanemethanol → (S)alpha-cyano-3-phenoxybenzyl(1R,cis)2,2-dimethyl-3-(cyclopropylmethoxycarbonylethynyl)-cyclopropane-carboxylate

HRID 1995167Notes

Reaction equation

HRID 1995167 reaction equation
[CH3:1][C:2]1([CH3:29])[C@@H:4]([C:5]#[C:6][C:7]([OH:9])=[O:8])[C@H:3]1[C:10]([O:12][C@H:13]([C:27]#[N:28])[C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([O:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:15]=1)=[O:11].[CH:30]1([CH2:33]O)[CH2:32][CH2:31]1>>[CH3:1][C:2]1([CH3:29])[C@@H:4]([C:5]#[C:6][C:7]([O:9][CH2:33][CH:30]2[CH2:32][CH2:31]2)=[O:8])[C@H:3]1[C:10]([O:12][C@H:13]([C:27]#[N:28])[C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([O:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:15]=1)=[O:11]

Participants

3

Reactant 2

HCID 75644CyclopropanemethanolHCID 13093796(S)alpha-cyano-3-phenoxy-benzyl (IR,cis) 2,2-dimethyl-3-(2-carboxyethynyl)-cyclopropane-carboxylate

Product 1

HCID 86739006(S)alpha-cyano-3-phenoxybenzyl(1R,cis)2,2-dimethyl-3-(cyclopropylmethoxycarbonylethynyl)-cyclopropane-carboxylate

Procedure

Using the procedure of Step A of Example 7, 1.4 g of (S)α-cyano-3-phenoxy-benzyl (1R,cis) 2,2-dimethyl-3-(2-carboxyethynyl)-cyclopropane-carboxylate and 0.3 ml of cyclopropylcarbinol were reacted and the product was chromatographed over silica gel. Elution with an 8-2 cyclohexane-ethyl acetate mixture yielded 1.5 g of (S)α-cyano-3-phenoxybenzyl (1R,cis) 2,2-dimethyl-3-(cyclopropylmethoxycarbonyl-ethynyl)-cyclopropane-carboxylate melting at 72° C.

Workup

  1. customwere reacted
  2. customthe product was chromatographed over silica gel
  3. washElution with an 8-2 cyclohexane-ethyl acetate mixture

Sources & evidence

ORD record
ord-9b2d62fef65b4190ac4660cdb440f5bc
Source dataset
uspto-grants-1983_09
Patent number
US04402972

Reaction notes

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