HCID 53936135, compound → HCID 70007361, compound

HRID 1265235Notes

Reaction equation

HRID 1265235 reaction equation
C[O:2][C:3](=[O:29])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]=[CH:11][C:12]2[C:21]([CH2:22][CH2:23][CH3:24])=[CH:20][C:19]3[C:18]([CH3:26])([CH3:25])[CH2:17][CH2:16][C:15]([CH3:28])([CH3:27])[C:14]=3[CH:13]=2)=[CH:6][CH:5]=1>C(OCC)(=O)C>[CH2:22]([C:21]1[C:12]([CH2:11][CH2:10][C:7]2[CH:8]=[CH:9][C:4]([C:3]([OH:29])=[O:2])=[CH:5][CH:6]=2)=[CH:13][C:14]2[C:15]([CH3:28])([CH3:27])[CH2:16][CH2:17][C:18]([CH3:25])([CH3:26])[C:19]=2[CH:20]=1)[CH2:23][CH3:24]

Participants

3

Reactant 1

HCID 53936135HCID 53936135, compound

Product 1

HCID 70007361HCID 70007361, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

4-[(3-n-Propyl-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl)carbonyl]benzoic acid methyl ester (2.7 mmol) in THF (25 mL) was treated with methyltriphenylphosphonium bromide/sodium azide (1.2 g, 3.1 mmol) and the solution was allowed to stir at ambient temperature for 3 h. The reaction was quenched with saturated aqueous NH4Cl and diluted with EtOAc. The organic solution was separated and washed with water and brine, dried (MgSO4), filtered, and concentrated to give a yellow oil. The crude product was crystallized (CH2Cl2/hexanes) to give 4-[(3-n-propyl-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl)ethenyl] benzoic acid methyl ester as white crystal (78%): TLC (20% ethyl acetate: 80% hexanes) Rf 0.8; mp 120-121° C.; 1H-NMR (400 MHz, CDCl3) δ7.94 (½ABq, J=8.0 Hz, 2H, ArH), 7.33 (½ABq, J=8.0 Hz, 2H, ArH), 7.09 (s, 1H, ArH), 7.08 (s, 1H, ArH), 5.80 (s, 1H, olefinic), 5.30 (s, 1H, olefinic), 3.90 (s, 3H, OCH3), 2.24 (t, J=8.0 Hz, 2H, CH2), 1.70 (s, 4H, 2CH2), 1.39 (m, 2H, CH2), 1.30 (s, 6H, 2CH3), 1.26 (s, 6H, 2CH3), 0.73 (t, J=7.5 Hz, 3H, CH3), Anal. (C27H34O2) C, H. The ester was hydrolized using the standard conditions of Example 1 to yield 4-[(3-n-propyl-5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)ethyl]benzoic acid (102). Crystallization gave white crystals (83%): TLC (10% MeOH-90% CHCl3) Rf 0.5; mp 263-265° C. 1H-NMR (400 MHz, CDCl3) δ8.00 (½ABq, J=8.0 Hz, 2H, ArH), 7.09 (s, 1H, ArH), 7.08 (s, 1H, ArH), 5.81 (s, 1H, olefinic), 5.31 (s, 1H, olefinic), 2.23 (t, J=8.0 Hz, 2H, CH2), 1.70 (s, 4H, 2CH2), 1.39 (m, 2H, CH2), 1.30 (s, 6H, 2CH3), 1.26 (s, 6H, 2CH3), 0.73 (t, J=7.5 Hz, 3H, CH3), FAB-MS m/z 377 (MH+); Anal. (C26H32O2) C, H.

Sources & evidence

ORD record
ord-60ca11d1dfde476f9e1eb35685377d06
Source dataset
uspto-grants-2003_04
Patent number
US06545049B1

Reaction notes

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