Tetrabutylammonium Fluoride Trihydrate → 3-Hydroxy-9H-xanthen-9-ylideneadamantane

HRID 1088481노트

반응식

HRID 1088481 반응식
[Si]([O:8][C:9]1[CH:10]=[CH:11][C:12]2[C:13](=[C:23]3[CH:30]4[CH2:31][CH:26]5[CH2:27][CH:28]([CH2:32][CH:24]3[CH2:25]5)[CH2:29]4)[C:14]3[C:19]([O:20][C:21]=2[CH:22]=1)=[CH:18][CH:17]=[CH:16][CH:15]=3)(C(C)(C)C)(C)C.[N+](CCCC)(CCCC)(CCCC)CCCC.[F-].O.O.O>C1COCC1.CCOCC>[OH:8][C:9]1[CH:10]=[CH:11][C:12]2[C:13](=[C:23]3[CH:30]4[CH2:31][CH:26]5[CH2:27][CH:28]([CH2:32][CH:24]3[CH2:25]5)[CH2:29]4)[C:14]3[C:19]([O:20][C:21]=2[CH:22]=1)=[CH:18][CH:17]=[CH:16][CH:15]=3

참가 물질

5

반응물 2

HCID 11726816Tetrabutylammonium Fluoride TrihydrateHCID 14645572HCID 14645572, 화합물

생성물 1

HCID 146455733-Hydroxy-9H-xanthen-9-ylideneadamantane수율 57.7%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매

실험 절차

The silylated alkene 5b (1.18 g, 2.6 mmol) was dissolved in 10 ml of THF. n-Bu4NF·3H2O (0.94 g, 3.0 mmol) was added and the yellow solution stirred for 30 min. The solution was then diluted with Et2O (100 mL), washed with H2O (200 mL), and the organic layer was concentrated. Recrystallization from ethyl acetate gave 0.48 g (1.5 mmol, 57.7%) of 5a as a white solid: 235°-240° C. (dec); 1H NMR (CDCl3) delta 1.873 (2, 10H), 1.992 (s, 2H), 3.472 (s, 1H), 3.529 (s, 1H), 6.70-6.76 (m, 2H), 6.96-7.04 (m, 2H), 7.06-7.14 (m, 2H), 7.21-7.29 (m, 2H); HRMS calc. 330.1621, found 330.1617; MS m/e (rel. intensity) 330 (100), 329 (43), 273 (37), 235 (16), 197 (11), 142 (65). Anal. calcd for C23H22O2 : C, 83.64; H, 6.67. Found; C, 83.75; H, 6.69. ##STR40##

후처리

  1. washwashed with H2O (200 mL)
  2. concentrationthe organic layer was concentrated
  3. customRecrystallization from ethyl acetate

출처 및 근거

ORD 기록
ord-73968ce5009b49a4b8255ae89cdfbf16
출처 데이터셋
uspto-grants-1990_10
특허 번호
US04962192

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