Triethylamine → Ethyl (2E,4E)-6-oxo-6-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthalenyl)-2,4-hexadienoate

HRID 356725Notes

Reaction equation

O[CH:2]([CH2:11][C:12](=[O:28])[C:13]1[C:22]([CH3:23])=[CH:21][C:20]2[C:19]([CH3:25])([CH3:24])[CH2:18][CH2:17][C:16]([CH3:27])([CH3:26])[C:15]=2[CH:14]=1)/[C:3](/C)=[CH:4]/[C:5]([O:7][CH2:8][CH3:9])=[O:6].C(N(CC)CC)C.CS(Cl)(=O)=O>C1COCC1>[O:28]=[C:12]([C:13]1[C:22]([CH3:23])=[CH:21][C:20]2[C:19]([CH3:25])([CH3:24])[CH2:18][CH2:17][C:16]([CH3:26])([CH3:27])[C:15]=2[CH:14]=1)/[CH:11]=[CH:2]/[CH:3]=[CH:4]/[C:5]([O:7][CH2:8][CH3:9])=[O:6]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 41 (0.33 g, 0.85 mmol) in 8 mL of THF at 0° C. was added triethylamine (0.5 mL, 4 mmol), and a solution of methylsulfonyl chloride (0.106 g, 0.93 mmol) in 2 mL of THF slowly. The mixture was stirred for 1 h at 0° C. and warmed to room temperature for 30 min. The mixture was filtered through a plug of silica gel with 10% ethyl acetate/hexane. The filtrate was concentrated to afford 42 as a light-yellow solid. Recrystallization from dichloromethane/hexane afforded the desired acid 42 as a yellow powder (0.3 g, 95%): m.p. 101°-102° C.; Rf 0.42 (10% ethyl acetate/hexane). The structure of the product was also confirmed using IR, 1H NMR and mass spectroscopy.

Workup

temperaturewarmed to room temperature for 30 min
filtrationThe mixture was filtered through a plug of silica gel with 10% ethyl acetate/hexane
concentrationThe filtrate was concentrated

Sources & evidence

ORD record: ord-85ec406437064d3992e6f96c53ffdafc
Source dataset: uspto-grants-1998_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05837725

Reaction notes

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