Acetyl chloride → (4-(6-Acetyloxy-1-benzothiophen-2-yl)phenyl) acetate

HRID 1937644Notes

Reaction equation

HRID 1937644 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12][C:11]3[CH:13]=[C:14]([OH:17])[CH:15]=[CH:16][C:10]=3[CH:9]=2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:25](Cl)(=[O:27])[CH3:26].[O:29]1CC[CH2:31][CH2:30]1>>[C:25]([O:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12][C:11]3[CH:13]=[C:14]([O:17][C:30](=[O:29])[CH3:31])[CH:15]=[CH:16][C:10]=3[CH:9]=2)=[CH:4][CH:3]=1)(=[O:27])[CH3:26]

Participants

5

Reactant 4

HCID 6367Acetyl chlorideHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 4459202-(4-Hydroxyphenyl)benzo(b)thiophen-6-ol

Product 1

HCID 9905410(4-(6-Acetyloxy-1-benzothiophen-2-yl)phenyl) acetate

Procedure

2-(4-Hydroxyphenyl)-6-hydroxybenzo[b]thiophene (2.42 g, 10 mmol) was dissolved in 100 mL of tetrahydrofuran and triethylamine (8 g, 100 mmol) was added. The reaction mixture was stirred under a nitrogen atmosphere at ambient temperature, while acetylchloride (2 g, 30 mmol) was slowly added. After sixteen hours, the reaction was terminated by the addition of water. The product began to crystallize at the interface, the water layer was discarded, and product crystallized out of the tetrahydrofuran layer. The product was filtered off and dried to give 2.06 of the title compound. 1H NMR: (d6-DMSO) δ 7.86 (s, 1H) 7.85 (d, 1H), 7.83 (s, 1H), 7.81 (d, 1H), 8.70 (d, 2H), 7.25 (d, 2H), 7.18 (dd, 1H). EA calculated for C18H14O4S: C, 66.24; H, 4.32 Found: C, 66.14; H, 4.38. MS(FD): m/e=326 (M+).

Workup

  1. additionwas slowly added
  2. waitAfter sixteen hours
  3. customthe reaction was terminated by the addition of water
  4. customto crystallize at the interface
  5. customproduct crystallized out of the tetrahydrofuran layer
  6. filtrationThe product was filtered off
  7. customdried

Sources & evidence

ORD record
ord-41f88278cc314c50a61d53603f6f74e9
Source dataset
uspto-grants-2002_05
Patent number
US06395769B1

Reaction notes

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