Neopentyl alcohol → (S)alpha-cyano-3-phenoxy-benzyl(1R,cis)2,2-dimethyl-3-[2-neopentyloxycarbonyl-ethynyl]-cyclopropane-carboxylate

HRID 1995173Notes

Reaction equation

HRID 1995173 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].[CH2:30](O)[C:31]([CH3:34])([CH3:33])[CH3:32]>>[CH3:1][C:2]1([CH3:29])[C@@H:4]([C:5]#[C:6][C:7]([O:9][CH2:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[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 6404Neopentyl alcoholHCID 13093796(S)alpha-cyano-3-phenoxy-benzyl (IR,cis) 2,2-dimethyl-3-(2-carboxyethynyl)-cyclopropane-carboxylate

Product 1

HCID 54365246(S)alpha-cyano-3-phenoxy-benzyl(1R,cis)2,2-dimethyl-3-[2-neopentyloxycarbonyl-ethynyl]-cyclopropane-carboxylateYield 82.8%

Procedure

Using the procedure of Step A of Example 15, 3.89 g of (S)α-cyano-3-phenoxy-benzyl (1R,cis) 2,2-dimethyl-3-(2-carboxyethynyl)-cyclopropane-carboxylate and 1 g of neopentyl alcohol were reacted and the mixture was stirred at room temperature for 4 hours and was filtered. The filtrate was washed with N hydrochloric acid, with water, dried and evaporated to dryness under reduced pressure. The residue was chromatographed over silica gel and was eluted with an 8-2 cyclohexane-ethyl acetate mixture to obtain 3.8 g of (S)α-cyano-3-phenoxy-benzyl (1R,cis) 2,2-dimethyl-3-[2-neopentyloxycarbonyl-ethynyl]-cyclopropane-carboxylate melting at 67° C.

Workup

  1. customwere reacted
  2. filtrationwas filtered
  3. washThe filtrate was washed with N hydrochloric acid, with water
  4. customdried
  5. customevaporated to dryness under reduced pressure
  6. customThe residue was chromatographed over silica gel
  7. washwas eluted with an 8-2 cyclohexane-ethyl acetate mixture

Sources & evidence

ORD record
ord-00f6b23aa4bd4b7bb1e426e0ee447f59
Source dataset
uspto-grants-1983_09
Patent number
US04402972

Reaction notes

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