Potassium Carbonate → (2Z,4E,6E)-2,6-Difluoro-3-methyl-7-(5,5,8,8-tetramethyl-3-propoxy-5,6,7,8-tetrahydro-naphthalen-2-yl)-nona-2,4,6-trienoic acid ethyl ester

HRID 1883283Notes

Reaction equation

HRID 1883283 reaction equation
[CH2:1]([O:3][C:4](=[O:31])[C:5]([F:30])=[C:6]([CH3:29])[CH:7]=[CH:8][C:9]([F:28])=[C:10]([C:13]1[C:22]([OH: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)[CH2:11][CH3:12])[CH3:2].C(O[C:35](=O)/[C:36](/F)=[C:37](\C)/C=C/C(/F)=C(\C1C(O)=CC2C(C)(C)CCC(C)(C)C=2C=1)/CC)C.C([O-])([O-])=O.[K+].[K+].C(I)CC>CC(C)=O>[CH2:1]([O:3][C:4](=[O:31])/[C:5](/[F:30])=[C:6](\[CH3:29])/[CH:7]=[CH:8]/[C:9](/[F:28])=[C:10](\[C:13]1[C:22]([O:23][CH2:35][CH2:36][CH3:37])=[CH:21][C:20]2[C:19]([CH3:24])([CH3:25])[CH2:18][CH2:17][C:16]([CH3:27])([CH3:26])[C:15]=2[CH:14]=1)/[CH2:11][CH3:12])[CH3:2]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 336431-IodopropaneHCID 86759479HCID 86759479, compoundHCID 86759481HCID 86759481, compound

Product 1

HCID 86759480(2Z,4E,6E)-2,6-Difluoro-3-methyl-7-(5,5,8,8-tetramethyl-3-propoxy-5,6,7,8-tetrahydro-naphthalen-2-yl)-nona-2,4,6-trienoic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Following General Procedure F and using 2,6-difluoro-7-(3-hydroxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-3-methyl-nona-2,4,6-trienoic acid ethyl ester (Intermediate 24, 2-E/Z mixture, 180 mg, 0.42 mmol), K2CO3 (290 mg, 2.1 mmol), and PrI (0.21 mL, 2.1 mmol) in acetone (2 mL), followed by HPLC (2.5% EtOAc-hexane) separation of the 2-E/Z product mixture, the title compound was obtained as a clear syrup (80 mg, 41%).

Workup

  1. customfollowed by HPLC (2.5% EtOAc-hexane) separation of the 2-E/Z product mixture

Sources & evidence

ORD record
ord-39e8d1ac62c946d5aa4882cf33c5e479
Source dataset
uspto-grants-2004_07
Patent number
US06759547B1

Reaction notes

Loading…