Trifluoroacetic acid → 3-acetyl-10,11-dihydro-5H-dibenzo(c,g)chromen-8(9H)-one

HRID 1431878노트

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HRID 1431878 반응식
C[Si]([C:5]#[C:6][C:7]1[CH:8]=[CH:9][C:10]2[C:19]3[CH:18]=[C:17]4[CH2:20][CH2:21][CH2:22][C:23](=[O:24])[C:16]4=[CH:15][C:14]=3[O:13][CH2:12][C:11]=2[CH:25]=1)(C)C.C(O)(C(F)(F)F)=[O:27]>>[C:6]([C:7]1[CH:8]=[CH:9][C:10]2[C:19]3[CH:18]=[C:17]4[CH2:20][CH2:21][CH2:22][C:23](=[O:24])[C:16]4=[CH:15][C:14]=3[O:13][CH2:12][C:11]=2[CH:25]=1)(=[O:27])[CH3:5]

참가 물질

3

반응물 2

HCID 6422Trifluoroacetic acidHCID 866883743-((trimethylsilyl)ethynyl)-10,11-dihydro-5H-dibenzo[c,g]chromen-8(9H)-one

생성물 1

HCID 866883753-acetyl-10,11-dihydro-5H-dibenzo(c,g)chromen-8(9H)-one수율 86%

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온도
65 °C

실험 절차

A 20 mL vial with stir bar was charged with 3-((trimethylsilyl)ethynyl)-10,11-dihydro-5H-dibenzo[c,g]chromen-8(9H)-one (850 mg, 2.44 mmol) and TFA (9.8 mL). The solution was heated to 65° C. After 3 h, the reaction was judged complete. The mixture was concentrated under reduced pressure; the resulting residue was taken up in CH2Cl2 and loaded onto a prepacked 25 g silica gel cartridge. The product was purified by chromatography on a prepacked 80 g silica gel column eluting with a solvent gradient from 5% to 85% EtOAc/hexanes. The product containing fractions were combined and concentrated to provide 3-acetyl-10,11-dihydro-5H-dibenzo[c,g]chromen-8(9H)-one (616 mg, 86%): 400 MHz 1H NMR (CDCl3) δ 8.00-7.94 (m, 1H), 7.81 (d, J=8.2 Hz, 1H), 7.77 (s, 1H), 7.64 (s, 2H), 5.16 (s, 2H), 2.98 (t, J=6.1 Hz, 2H), 2.69-2.64 (m, 2H), 2.63 (s, 3H), 2.21-2.09 (m, 2H).

후처리

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customThe product was purified by chromatography on a prepacked 80 g silica gel column
  3. washeluting with a solvent gradient from 5% to 85% EtOAc/hexanes
  4. additionThe product containing fractions
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-07afdee382cf4bfd968692298878326e
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08940718B2

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