Dicyclohexylcarbodiimide → (S)alpha-cyano-3-phenoxy-benzyl (1R,trans) 2,2-dimethyl-3-(1,2-propadienyl)-cyclopropane-carboxylate

HRID 485709Notes

Reaction equation

C1(N=C=NC2CCCCC2)CCCCC1.[CH3:16][C:17]1([CH3:26])[C@H:19]([CH:20]=[C:21]=[CH2:22])[C@H:18]1[C:23]([OH:25])=[O:24].[C:27]([C@@H:29](O)[C:30]1[CH:35]=[CH:34][CH:33]=[C:32]([O:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[CH:31]=1)#[N:28]>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH3:16][C:17]1([CH3:26])[C@H:19]([CH:20]=[C:21]=[CH2:22])[C@H:18]1[C:23]([O:25][C@H:29]([C:27]#[N:28])[C:30]1[CH:35]=[CH:34][CH:33]=[C:32]([O:36][C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)[CH:31]=1)=[O:24]

Participants

Conditions

Temperature: 0 °C

Procedure

1.22 g of dicyclohexylcarbodiimide and a few crystals of 4-dimethylamino-pyridine were added at 0° C. to a solution of 900 mg of (1R,trans) 2,2-dimethyl-3-(1,2-propadienyl)cyclopropane-carboxylic acid in 20 ml of methylene chloride and the mixture was stirred at 0° C. for 15 minutes. A solution of 1.46 g of (S)α-cyano-3-phenoxy-benzyl alcohol in 7 ml of methylene chloride was added to the mixture which was stirred for 5 hours at 20° C. and then filtered. The filtrate was evaporated to dryness under reduced pressure and the residue was chromatographed over silica gel. Elution with a 6-4 and then a 7-3 benzene-petroleum ether (b.p.=35° to 70° C.) mixture yielded 754 mg of (S)α-cyano-3-phenoxy-benzyl (1R,trans) 2,2-dimethyl-3-(1,2-propadienyl)-cyclopropane-carboxylate with a specific rotation of [α]D20 =-25° (c=0.7% in chloroform).

Workup

stirringwas stirred for 5 hours at 20° C.
filtrationfiltered
customThe filtrate was evaporated to dryness under reduced pressure
customthe residue was chromatographed over silica gel
washElution with a 6-4

Sources & evidence

ORD record: ord-ddb0141353724446b22281f0fac1fb72
Source dataset: uspto-grants-1985_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04537897

Reaction notes

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