Tetrahydrofuran → 3-[4-(2-Diethylaminoethoxy)benzoyl]-6-hydroxy-2-(4-hydroxyphenyl)benzo[b]thiophene

HRID 2198610Notes

Reaction equation

HRID 2198610 reaction equation
Cl.[CH2:2]([N:4]([CH2:41][CH3:42])[CH2:5][CH2:6][O:7][C:8]1[CH:40]=[CH:39][C:11]([C:12]([C:14]2[C:15]3[CH:33]=[CH:32][C:31]([O:34]S(C)(=O)=O)=[CH:30][C:16]=3[S:17][C:18]=2[C:19]2[CH:24]=[CH:23][C:22]([O:25]S(C)(=O)=O)=[CH:21][CH:20]=2)=[O:13])=[CH:10][CH:9]=1)[CH3:3].O1CCCC1.[OH-].[Na+]>CO>[CH2:41]([N:4]([CH2:2][CH3:3])[CH2:5][CH2:6][O:7][C:8]1[CH:40]=[CH:39][C:11]([C:12]([C:14]2[C:15]3[CH:33]=[CH:32][C:31]([OH:34])=[CH:30][C:16]=3[S:17][C:18]=2[C:19]2[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=2)=[O:13])=[CH:10][CH:9]=1)[CH3:42]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 1317128673-[4-(2-Diethylaminoethoxy)benzoyl]-6-methanesulfonyloxy-2-(4-methanesulfonyloxyphenyl)benzo[b]thiophene, hydrochloride

Product 1

HCID 152892393-[4-(2-Diethylaminoethoxy)benzoyl]-6-hydroxy-2-(4-hydroxyphenyl)benzo[b]thiophene

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 4 g. portion of the product of Example 6 above was added to 100 ml. of tetrahydrofuran, 40 ml. of methanol and 10 ml. of 5 N sodium hydroxide, and the mixture was stirred at ambient temperature for 24 hours. The volatile portions were then evaporated under vacuum, and the product was worked up as described above in Example 19. The yellow solid obtained was dried, and was purified by chromatography as described above in Example 20. The process gave 2.0 g. of a yellow foam, which was identified as the expected product by its nmr spectrum (taken in dmso-d6 at 100 mHz): δ0.93 (6H, t, J=7 Hz, CH2CH3); 2.50 (4H, q, J=7 Hz, CH2CH3); 2.72 (2H, t, J=6 Hz, NCH2); 4.01 (2H, t, J=6 Hz, OCH2CH2N); 6.67 (2H, d, J=9 Hz aromatic o to OH); 6.85 (1H, q, JH4-H5 =9 Hz, JH5-H7 =2 Hz, H5 of benzothiophene ring); 6.88 (2H, d, J=9 Hz, aromatic o to OCH2); 7.18 (2H, d, J=9 Hz, aromatic m to OH); 7.27 (1H, d, J=9 Hz, H4 of benzothiophene ring); 7.34 (1H, d, J=2 Hz, H7 of benzothiophene ring); 7.66 (2H, d, J=9 Hz, aromatic o to CO); 9.72 (2H, broad s, OH). High resolution mass spectrum: calculated for C27H27NO4S: 461.16607, found 461.16551; Ultraviolet spectrum λmax (ε) taken in ethanol 290 cm (34,000); infrared absorption in KBr at 1608 cm-1 attributable to the eneone system.

Workup

  1. customThe volatile portions were then evaporated under vacuum
  2. customThe yellow solid obtained
  3. customwas dried
  4. customwas purified by chromatography
  5. customThe process gave 2.0 g

Sources & evidence

ORD record
ord-2df768a116db42d59745aca18a92c25b
Source dataset
uspto-grants-1982_11
Patent number
US04358593

Reaction notes

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