Sodium Hydroxide → HCID 9863994, compound

HRID 1018110Notes

Reaction equation

HRID 1018110 reaction equation
C[O:2][C:3](=[O:27])[C:4]1[CH:9]=[CH:8][C:7]([C:10]#[C:11][C:12]2[CH:13]=[CH:14][C:15]3[C:21]([CH2:23][O:24][CH3:25])([CH3:22])[CH2:20][CH2:19][CH2:18][S:17][C:16]=3[CH:26]=2)=[CH:6][CH:5]=1.[OH-].[Na+]>C1COCC1.C(O)C>[CH3:25][O:24][CH2:23][C:21]1([CH3:22])[CH2:20][CH2:19][CH2:18][S:17][C:16]2[CH:26]=[C:12]([C:11]#[C:10][C:7]3[CH:6]=[CH:5][C:4]([C:3]([OH:27])=[O:2])=[CH:9][CH:8]=3)[CH:13]=[CH:14][C:15]1=2

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 70002054HCID 70002054, compound

Product 1

HCID 9863994HCID 9863994, compoundYield 92.7%

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

316 mg (0.83 mmol) of 4-(5-methoxymethyl-5-methyl-2,3,4,5-tetrahydrobenzo[b]thiepin-8-ylethynyl)-benzoic acid methyl ester was dissolved in 8 ml of THF/EtOH (1/1) and treated with 1.38 ml of 3N NaOH (5 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/ HCl, extracted twice with diethylether, the organic phase was washed with brine, dried over magnesium sulfate, filtrated and evaporated to dryness. Crystallization of the residue from hexane/ethylacetate yielded 282 mg of the title product as white crystals of m.p. 182-183° C.

Workup

  1. additionThe mixture was then poured
  2. extractionextracted twice with diethylether
  3. washthe organic phase was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltrated
  6. customevaporated to dryness
  7. customCrystallization of the residue from hexane/ethylacetate

Sources & evidence

ORD record
ord-fa1b937dd070461f98210175be22a3e5
Source dataset
uspto-grants-2002_11
Patent number
US06479670B1

Reaction notes

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