HCID 73858727, compound → HCID 22005205, compound

HRID 324864Notes

Reaction equation

HRID 324864 reaction equation
[CH:1]([CH:4]1[C:9](CO)([C:10](OCC)=[O:11])[C:8]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[C:23]#[CH:24])=[C:7]([CH:25]=[CH:26][CH2:27][CH2:28][CH3:29])[C:6]([CH:30]([CH3:32])[CH3:31])=[N:5]1)([CH3:3])[CH3:2]>C(OCC)(=O)C.CCCCCC>[CH:1]([C:4]1[C:9]([CH2:10][OH:11])=[C:8]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[CH:23]=[CH2:24])[C:7]([CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])=[C:6]([CH:30]([CH3:31])[CH3:32])[N:5]=1)([CH3:3])[CH3:2]

Participants

3

Reactant 1

HCID 73858727HCID 73858727, compound

Product 1

HCID 22005205HCID 22005205, compound

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

The title compound was prepared from ethyl 2,6-diisopropyl-3-hydroxymethyl-4-(2-ethynylphenyl)-5-(pent-1-enyl)pyridine-3-carboxylate by the procedure described in Example 125, Step F. 1H NMR (300 MHz, CDCl3) (reported as a mixture of olefin isomers): δ 0.60-0.90 (m, 3 H), 1.0-1.40 (m, 15 H), 1.60-1.90 (m, 2 H), 3.20-3.50 (m, 2 H), 4.20-4.40 (m, 2 H), 5.14 (dt, J=11.0, 1.0 Hz, 1 H), 5.40 (m, 1 H), 5.90 (m, 1 H), 6.30 (m, 1 H), 7.0-7.70 (m, 4 H). FAB-MS: calculated for C25H33NO 363.5; found 364 (M+H, 100%). Rf 0.28 (10% ethyl acetate/n-hexane).

Sources & evidence

ORD record
ord-151c16652f604ed38318e3e0869de524
Source dataset
uspto-grants-2001_04
Patent number
US06218431B1

Reaction notes

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