Lithium hydroxide, monohydrate → 4-[(7,8-Dihydro-8,8-dimethyl-5-(2-thiazolyl)naphth-3-yl)ethynyl]benzoic acid

HRID 1417669Notes

Reaction equation

HRID 1417669 reaction equation
[CH3:1][C:2]1([CH3:30])[CH2:11][CH:10]=[C:9]([C:12]2[S:13][CH:14]=[CH:15][N:16]=2)[C:8]2[CH:7]=[C:6]([C:17]#[C:18][C:19]3[CH:29]=[CH:28][C:22]([C:23]([O:25]CC)=[O:24])=[CH:21][CH:20]=3)[CH:5]=[CH:4][C:3]1=2.O[Li].O>C1COCC1.O>[CH3:1][C:2]1([CH3:30])[CH2:11][CH:10]=[C:9]([C:12]2[S:13][CH:14]=[CH:15][N:16]=2)[C:8]2[CH:7]=[C:6]([C:17]#[C:18][C:19]3[CH:20]=[CH:21][C:22]([C:23]([OH:25])=[O:24])=[CH:28][CH:29]=3)[CH:5]=[CH:4][C:3]1=2

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 15430593Ethyl 4-[(5,6-dihydro-5,5-dimethyl-8-(2-thiazolyl)-2-naphthalenyl)ethynyl]benzoate2×

Product 1

HCID 223237374-[(7,8-Dihydro-8,8-dimethyl-5-(2-thiazolyl)naphth-3-yl)ethynyl]benzoic acid

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

A solution of 33.9 mg (0.08 mmol) of ethyl 4-[(5,6-dihydro-5,5-dimethyl-8-(2-thiazolyl)-2-naphthalenyl)ethynyl]benzoate (Compound 15a) and 8.5 mg (0.20 mmol) of LiOH-H2O in 3 ml of THF/water (3:1, v/v), was stirred overnight at room temperature. The reaction was quenched by the addition of sat. aqueous NH4Cl and extracted with EtOAc. The combined organic layers were washed with water and brine, dried over Na2SO4 and concentrated in vacuo to give the title compound as a colorless solid. PMR (d6 -DMSO): δ 1.29 (6H, s), 2.42 (2H, d, J=4.6 Hz), 6.68 (1H, t, J=4.6 Hz), 7.51 (2H, m), 7.62 (2H, d, J=8.2 Hz), 7.77 (1H, d, J=3.3 Hz), 7.93 (2H, d, J=8.2 Hz), 7.98 (1 H, d, J=3.3 Hz).

Workup

  1. customThe reaction was quenched by the addition of sat. aqueous NH4Cl
  2. extractionextracted with EtOAc
  3. washThe combined organic layers were washed with water and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e4b919a47a2a41bfbdbd143bda427324
Source dataset
uspto-grants-1999_03
Patent number
US05877207

Reaction notes

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