Sodium Hydroxide → HCID 9951935, compound

HRID 1018112Notes

Reaction equation

HRID 1018112 reaction equation
C[O:2][C:3](=[O:28])[C:4]1[CH:9]=[CH:8][C:7](/[CH:10]=[CH:11]/[C:12]2[CH:13]=[CH:14][C:15]3[C:21]([CH2:23][O:24][CH2:25][CH3:26])([CH3:22])[CH2:20][CH2:19][CH2:18][S:17][C:16]=3[CH:27]=2)=[CH:6][CH:5]=1.[OH-].[Na+]>C1COCC1.C(O)C>[CH2:25]([O:24][CH2:23][C:21]1([CH3:22])[CH2:20][CH2:19][CH2:18][S:17][C:16]2[CH:27]=[C:12](/[CH:11]=[CH:10]/[C:7]3[CH:6]=[CH:5][C:4]([C:3]([OH:28])=[O:2])=[CH:9][CH:8]=3)[CH:13]=[CH:14][C:15]1=2)[CH3:26]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 70002930HCID 70002930, compound

Product 1

HCID 9951935HCID 9951935, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

406 mg (0.99 mmol) of (E)-4-[2-(5-ethoxymethyl-5-methyl-2,3,4,5-tetrahydrobenzo[b]thiepin-8-yl)-vinyl]-benzoic acid methyl ester was dissolved in 4 ml of THF/ethanol=1/1 and treated with 1.32 ml of 3N NaOH(4 eq). The reaction flask was kept in the dark and stirring continued for 18 h at room temperature. The mixture was then poured onto crushed ice/diluted HCl, extracted twice with ethylacetate, the organic phase was washed with a small amount of water, dried over magnesium sulfate, filtrated and the solvent evaporated. Crystallization of the residue from hexane/ethylacetate (8/2) yielded 337 mg of the title compound as white crystals of m.p. 186-187° C.

Workup

  1. additionThe mixture was then poured
  2. customonto crushed ice/diluted HCl
  3. extractionextracted twice with ethylacetate
  4. washthe organic phase was washed with a small amount of water
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltrated
  7. customthe solvent evaporated
  8. customCrystallization of the residue from hexane/ethylacetate (8/2)

Sources & evidence

ORD record
ord-3adb1f8ed4954359b3cd975772ecb220
Source dataset
uspto-grants-2002_11
Patent number
US06479670B1

Reaction notes

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