Dicyclohexylcarbodiimide → Allyl 4-{[1-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)ethyloxy]carbonyl}benzoate

HRID 2294592Notes

Reaction equation

HRID 2294592 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[CH3:16][C:17]1([CH3:32])[CH2:26][CH2:25][C:24]([CH3:28])([CH3:27])[C:23]2[CH:22]=[C:21]([CH:29]([OH:31])[CH3:30])[CH:20]=[CH:19][C:18]1=2.[C:33]([O:44][CH2:45][CH:46]=[CH2:47])(=[O:43])[C:34]1[CH:42]=[CH:41][C:37]([C:38]([O-])=[O:39])=[CH:36][CH:35]=1.ClCCl.CCCCCC>CN(C)C1C=CN=CC=1.C1COCC1.ClCCl>[CH3:32][C:17]1([CH3:16])[CH2:26][CH2:25][C:24]([CH3:27])([CH3:28])[C:23]2[CH:22]=[C:21]([CH:29]([O:31][C:38]([C:37]3[CH:41]=[CH:42][C:34]([C:33]([O:44][CH2:45][CH:46]=[CH2:47])=[O:43])=[CH:35][CH:36]=3)=[O:39])[CH3:30])[CH:20]=[CH:19][C:18]1=2

Participants

8

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 21226440Methylenechloride HexaneHCID 214744991-(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)ethanolHCID 713443804-{[(Prop-2-en-1-yl)oxy]carbonyl}benzoate

Product 1

HCID 21474484Allyl 4-{[1-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)ethyloxy]carbonyl}benzoate

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

1.54 g (7.44 mmol) of dicyclohexylcarbodiimide and 0.91 g of 4-dimethylaminopyridine are added to a solution of 1.73 g (7.44 mmol) of (+)-1-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)ethyl alcohol and 1.54 g (7.44 mmol) of allyl monoterephthalate in 50 ml of THF. The reaction medium is left stirring at room temperature for 3 h. After treatment and chromatography on silica in dichloromethane, 2.42 g (77%) of the expected derivative are isolated in the form of a colorless oil (Rf=0.46; dichloromethane/hexane, 50:50).

Workup

  1. waitThe reaction medium is left

Sources & evidence

ORD record
ord-e5380edb8df040ed8181d93cb2a49015
Source dataset
uspto-grants-1997_11
Patent number
US05688817

Reaction notes

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