4-Phenylcyclohexyl 4-methylbenzenesulfonate → HCID 178419141, compound

HRID 1259470Notes

Reaction equation

HRID 1259470 reaction equation
[CH:1]1([PH:6][CH:7]2[CH2:11][CH2:10][CH2:9][CH2:8]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[BH3:12].C([Li])CCC.CC1C=CC(S(O[CH:29]2[CH2:34][CH2:33][CH:32]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[CH2:31][CH2:30]2)(=O)=O)=CC=1>>[CH:7]1([P:6]([CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5]2)[CH:38]2[CH2:37][CH2:36][CH:35]([C:32]3[CH:33]=[CH:34][CH:29]=[CH:30][CH:31]=3)[CH2:40][CH2:39]2)[CH2:8][CH2:9][CH2:10][CH2:11]1.[BH3:12]

Participants

4

Reactant 3

HCID 135868944-Phenylcyclohexyl 4-methylbenzenesulfonateHCID 178418339ButyllithiumHCID 178419150HCID 178419150, compound

Product 1

HCID 178419141HCID 178419141, compound

Procedure

The product is made similarly to its analog in Example 1 from dicyclopentyl-phosphine-borane (10.6 g; 57.5 mmol.), n-butyl lithium (39.5 mL of 1.6 M solution; 63.3 mmol.) and 4-phenylcyclohexyl 4-methylbenzenesulfonate (22.8 g; 68.9 mmol.). Yield 14.5 g (74%). 31P{1H} NMR (δ, C6D6, ppm): 33.22 and 33.83 (broad); 1H NMR (δ, C6D6, ppm): 0.944 (m, 3H, BH3), 1.2-2.2 (m, 27H, cyclopentyl+cyclohexyl), 2.82 (m, 1H, PhCH), 7.0-7.25 (m, 5H, Ph).

Sources & evidence

ORD record
ord-8bd30be6265f4771953abb47a08b3a3b
Source dataset
uspto-grants-2013_06
Patent number
US08466306B2

Reaction notes

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