Methyl iodide → 4,4'-Dipentyl-4-prop-1-ynylbicyclohexyl

HRID 380255Notes

Reaction equation

HRID 380255 reaction equation
[CH2:1]([Li])CCC.[C:6]([C:8]1([CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH2:13][CH2:12][CH:11]([CH:14]2[CH2:19][CH2:18][CH:17]([CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH2:16][CH2:15]2)[CH2:10][CH2:9]1)#[CH:7].IC.CN1CCCN(C)C1=O>CCCCCC.C1COCC1>[CH2:25]([C:8]1([C:6]#[C:7][CH3:1])[CH2:9][CH2:10][CH:11]([CH:14]2[CH2:19][CH2:18][CH:17]([CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH2:16][CH2:15]2)[CH2:12][CH2:13]1)[CH2:26][CH2:27][CH2:28][CH3:29]

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-HCID 154519764-Ethynyl-4,4'-dipentylbicyclohexylHCID 178418339Butyllithium

Product 1

HCID 154519774,4'-Dipentyl-4-prop-1-ynylbicyclohexyl

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

9.66 ml of a 15% solution of n-butyllithium in hexane are added dropwise at −70° C. to 4.80 g of 4-ethynyl-4,4′-dipentylbicyclohexyl in 40 ml of THF, and the mixture is stirred for 15 minutes. A solution of 0.99 ml of iodomethane and 1.914 ml of 1,3-dimethyltetrahydro-2-pyrimidinone in 10 ml of THF is subsequently added dropwise to the reaction solution at this temperature, and the cooling is removed. Conventional work-up gives 4,4′-dipentyl-4-prop-1-ynylbicyclohexyl (C 35 N 35.4 I, Δε−1.54, Δn 0.01).

Workup

  1. customthe cooling is removed

Sources & evidence

ORD record
ord-b0135a888f6647fa960c31c4515352b0
Source dataset
uspto-grants-2001_10
Patent number
US06303194B1

Reaction notes

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