1-Pentanol → tert.-butyl(1R,cis)2,2-dimethyl-3-[pentyloxycarbonylethynyl]cyclopropane-carboxylate

HRID 464455Notes

Reaction equation

HRID 464455 reaction equation
[CH3:1][C:2]1([CH3:17])[C@@H:4]([C:5]#[C:6][C:7]([OH:9])=[O:8])[C@H:3]1[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11].[CH3:18][CH2:19][CH2:20][CH2:21][CH2:22]O>>[CH3:1][C:2]1([CH3:17])[C@@H:4]([C:5]#[C:6][C:7]([O:9][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[O:8])[C@H:3]1[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11]

Participants

3

Reactant 2

HCID 62761-PentanolHCID 13093787Tert.-butyl(1R,cis)2,2-dimethyl-3-(carboxy ethynyl)cyclopropane-carboxylate

Product 1

HCID 57192866tert.-butyl(1R,cis)2,2-dimethyl-3-[pentyloxycarbonylethynyl]cyclopropane-carboxylate

Procedure

Using the procedure of Step A of Example 7, 3 g of tert.-butyl(1R,cis)2,2-dimethyl-3-(2-carboxyethynyl)-cyclopropane-carboxylate and 2 ml of n-amyl alcohol were reacted and the residue was chromatographed over silica gel. Elution with an 8-2 hexane-isopropyl ether mixture yielded 2.7 g of tert.-butyl(1R,cis)2,2-dimethyl-3-[pentyloxycarbonylethynyl]cyclopropane-carboxylate.

Workup

  1. customwere reacted
  2. customthe residue was chromatographed over silica gel
  3. washElution with an 8-2 hexane-isopropyl ether mixture

Sources & evidence

ORD record
ord-555f49f8eb014fd9a81f51cb927b6fbb
Source dataset
uspto-grants-1985_10
Patent number
US04547522

Reaction notes

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