Hydrochloric Acid → HCID 15870513, compound

HRID 1600593Notes

Reaction equation

HRID 1600593 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2[S:13][C:12]3[CH:14]=[CH:15][CH:16]=[CH:17][C:11]=3[C:10]=2[O:18][C:19]2[CH:24]=[CH:23][C:22]([O:25]CC3C=CC=CC=3)=[CH:21][CH:20]=2)[CH:6]=[CH:7][CH:8]=1.Cl>CCO.CCOC(C)=O.[Pd]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2[S:13][C:12]3[CH:14]=[CH:15][CH:16]=[CH:17][C:11]=3[C:10]=2[O:18][C:19]2[CH:20]=[CH:21][C:22]([OH:25])=[CH:23][CH:24]=2)[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 15872362HCID 15872362, compound

Product 1

HCID 15870513HCID 15870513, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584252Ethanol ethylacetateSolvent

Procedure

To a solution of 2-(3-methoxyphenyl)-3-(4-benzyloxyphenoxy)benzo[b]thiophene (8.30 g, 29.0 mmol) in 1:1 (100 mL) EtOH/EtOAc in a Paar bottle was added 10% Pd/C (4.0 g). To this suspension was added 2.0 mL of con. HCl. The resulting mixture was hydrogenated at 40 psi for 20 min. The reaction was filtered through Celite®, and the filtrate was concentrated in vacuo to an oil. The crude product was partitioned between CHCl3 and sat. NaHCO3 solution. The layers were separated, and the organic was dried (Na2SO4) and concentrated in vacuo to give 3.8 g (61%) of 2-(3-methoxyphenyl)-3-(4-hydroxyphenoxy)benzo[b]thiophene as an amber brown foam. 1H NMR (CDCl3) d 7.80 (d, J=8.1 Hz, 1H), 7.46-7.27 (m, 6H), 6.88-6.84 (m, 3H), 6.71-6.74 (m, 2H), 4.57 (s, 1H), 3.77 (s, 3H). FD mass spec: 348. Anal. Calcd. for C21H16O3S: C, 72.39; H, 4.63. Found: C, 72.10; H, 4.63.

Workup

  1. additionTo this suspension was added 2.0 mL of con
  2. filtrationThe reaction was filtered through Celite®
  3. concentrationthe filtrate was concentrated in vacuo to an oil
  4. customThe crude product was partitioned between CHCl3 and sat. NaHCO3 solution
  5. customThe layers were separated
  6. dry with materialthe organic was dried (Na2SO4)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-04d40b6b1b5d498e922bab927f8e9201
Source dataset
uspto-grants-1999_11
Patent number
US05977098

Reaction notes

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