Sodium Hydroxide → HCID 88113875, compound

HRID 398313Notes

Reaction equation

HRID 398313 reaction equation
[CH2:1]([O:5][C:6]1[C:20](/[CH:21]=[CH:22]/[CH:23]=[CH:24]/[C:25](/[CH3:32])=[CH:26]/[C:27]([O:29]CC)=[O:28])=[CH:19][C:9]2[C:10]3([CH3:18])[CH:15]([OH:16])[C:14]([CH3:17])([C:8]=2[CH:7]=1)[CH2:13][CH2:12][CH2:11]3)[CH2:2][CH2:3][CH3:4].[OH-].[Na+]>C(O)C.C1COCC1>[CH2:1]([O:5][C:6]1[C:20](/[CH:21]=[CH:22]/[CH:23]=[CH:24]/[C:25](/[CH3:32])=[CH:26]/[C:27]([OH:29])=[O:28])=[CH:19][C:9]2[C:10]3([CH3:18])[CH:15]([OH:16])[C:14]([CH3:17])([C:8]=2[CH:7]=1)[CH2:13][CH2:12][CH2:11]3)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 88328679HCID 88328679, compound

Product 1

HCID 88113875HCID 88113875, compound

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

This ester was dissolved in 7 ml of ethanol/THF=1/1 and treated under argon with 2.1 ml of 2N NaOH. The mixture was left to react at room temperature for 64 h. and then poured into ice/HCl/ethyl acetate. The organic phase was washed twice with water, dried and evaporated. Recrystallization from hexane/ethyl acetate=7/3 yielded 153 mg of (2E,4E,6E)-(5RS,9SR,10RS)-7-(3-butoxy-10-hydroxy-5,9-dimethyl-6,7,8,9-tetrahydro-5,9-methano-5H-benzocyclohepten-2-yl)-3-methyl-hepta-2,4,6-trienoic acid as yellow crystals of m.p. 176-178°.

Workup

  1. waitThe mixture was left
  2. customto react at room temperature for 64 h.
  3. washThe organic phase was washed twice with water
  4. customdried
  5. customevaporated
  6. customRecrystallization from hexane/ethyl acetate=7/3

Sources & evidence

ORD record
ord-4d56affb1b694920b117cd22fdb0482e
Source dataset
uspto-grants-2003_08
Patent number
US06610877B1

Reaction notes

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