Sodium Hydroxide → (2Z,4E,6E)-2,6-Difluoro-7-(3-methoxymethoxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-3-methyl-nona-2,4,6-trienoic acid

HRID 1883280Notes

Reaction equation

HRID 1883280 reaction equation
C([O:3][C:4](=[O:34])/[C:5](/[F:33])=[C:6](\[CH3:32])/[CH:7]=[CH:8]/[C:9](/[F:31])=[C:10](\[C:13]1[C:22]([O:23][CH2:24][O:25][CH3:26])=[CH:21][C:20]2[C:19]([CH3:28])([CH3:27])[CH2:18][CH2:17][C:16]([CH3:30])([CH3:29])[C:15]=2[CH:14]=1)/[CH2:11][CH3:12])C.[OH-].[Na+]>CCO>[F:33]/[C:5](=[C:6](/[CH3:32])\[CH:7]=[CH:8]\[C:9](\[F:31])=[C:10](/[C:13]1[C:22]([O:23][CH2:24][O:25][CH3:26])=[CH:21][C:20]2[C:19]([CH3:28])([CH3:27])[CH2:18][CH2:17][C:16]([CH3:30])([CH3:29])[C:15]=2[CH:14]=1)\[CH2:11][CH3:12])/[C:4]([OH:34])=[O:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 12146422(2Z,4E,6E)-2,6-difluoro-7-(3-methoxymethoxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-3-methyl-nona-2,4,6-trienoic acid ethyl ester2×

Product 1

HCID 12146423(2Z,4E,6E)-2,6-Difluoro-7-(3-methoxymethoxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-3-methyl-nona-2,4,6-trienoic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Following General Procedure E and using (2Z,4E,6E)-2,6-difluoro-7-(3-methoxymethoxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-3-methyl-nona-2,4,6-trienoic acid ethyl ester (Compound 20, 314 mg, 0.66 mmol), 1M NaOH (2.0 mL) and EtOH (5 mL) at 40° C. for overnight followed by flash column chromatography on silica gel (10%→50% EtOAc-hexane), the title compound was obtained as a yellow solid (282 mg, 95%). 1H NMR (300 MHz, CDCl3): δ0.98 (t, J=7.6 Hz, 3H), 1.23 (s, 6H), 1.29 (s, 6H), 1.67 (s, 4H), 2.06 (d, J=3.2 Hz, 3H), 2.47 (m, 1H), 2.68 (m, 1H), 3.44 (s, 3H), 5.12 (s, 2H), 6.35 (dd, J=26.1, 15.8 Hz, 1H), 6.94 (s, 1H), 7.01 (dd, J=15.8, 1.8 Hz, 1H), 7.02 (s, 1H).

Workup

  1. customat 40° C.
  2. customfor overnight

Sources & evidence

ORD record
ord-2ae6f80c15164b4a985ff6af1a66ba7d
Source dataset
uspto-grants-2004_07
Patent number
US06759547B1

Reaction notes

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