Hydroxide → HCID 18687861, compound

HRID 1873150Notes

Reaction equation

HRID 1873150 reaction equation
C[O:2][C:3]([CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[C:22]3[C:23]4[CH:29]=[CH:28][CH:27]=[CH:26][C:24]=4[S:25][C:21]=3[CH:20]=[C:19]3[C:14]=2[CH:15]=[CH:16][C:17]([O:30][CH2:31][C:32]([O:34]C)=[O:33])=[CH:18]3)=[CH:9][CH:8]=1)=[O:4].[OH-]>O1CCCC1.CO>[C:3]([CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[C:22]3[C:23]4[CH:29]=[CH:28][CH:27]=[CH:26][C:24]=4[S:25][C:21]=3[CH:20]=[C:19]3[C:14]=2[CH:15]=[CH:16][C:17]([O:30][CH2:31][C:32]([OH:34])=[O:33])=[CH:18]3)=[CH:9][CH:8]=1)([OH:4])=[O:2]

Participants

5

Reactant 2

HCID 961Hydroxide2×HCID 86755707HCID 86755707, compound

Product 1

HCID 18687861HCID 18687861, compoundYield 71.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of [11-(4-methoxycarbonylmethoxy-phenyl)-benzo [b]naphtho[2,3-d]thiophen-8-yloxy]-acetic acid, methyl ester (0.268 g, 0.551 mmol) in tetrahydrofuran (8 mL) and methanol (5 mL) was added an aqueous solution of potassuim hydroxide (1 N, 2.2 mL, 2.2 mmol) dropwise at room temperature. After stirring 2 hours an addition of potassuim hydroxide (1 N, 1 mL, 1 mmol) was introduced. After stirring another 14 hours the solvents were removed and the residue was disolved in water (50 mL) and was acidified with 10% aqueous hydrochloric acid, and the organics were extracted with diethyl ether. The solvent was removed and chased with benzene and petroleum ether and dried at 53° C. to give the title compound as a white solid (0.18 g, 43%): mp 245-246° C.; NMR (DMSO-d6); δ13.08 (broad s, 2 H), 8.44 (s, 1 H), 7.93 (d, J=8 Hz, 1 H), 7.45 - 7.35 (m, 3 H), 7.31 (d, J=9 Hz, 2 H), 7.22 (d, J=9 Hz, 2 H), 7.17 (dd, J=3,9 Hz, 1 H), 7.10 (ddd, J=9, 9, 1 Hz, 1 H), 6.67 (d, J=8 Hz, 1 H), 4.84 (d, J=7 Hz, 4 H); MS (EI): [M+] 458; Anal. Calc. for C26 H18O6S: C, 68.11, H, 3.96, N, 0.00. Found: C, 66.41, H, 3.95, N, 0.05.

Workup

  1. additionwas introduced
  2. stirringAfter stirring another 14 hours the solvents
  3. customwere removed
  4. extractionthe organics were extracted with diethyl ether
  5. customThe solvent was removed
  6. customdried at 53° C.

Sources & evidence

ORD record
ord-6c7f8ff01710418da0a3b451bb4a83b5
Source dataset
uspto-grants-2000_08
Patent number
US06110962

Reaction notes

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