Triacetoxyperiodinane → Methyl 5-acetyl-4-(adamantan-1-ylmethoxy)-2-fluorobenzoate

HRID 1849731노트

반응식

HRID 1849731 반응식
[C:1]12([CH2:11][O:12][C:13]3[C:22]([CH:23]([OH:25])[CH3:24])=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[C:15]([F:26])[CH:14]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>ClCCl.C(OCC)C>[C:23]([C:22]1[C:13]([O:12][CH2:11][C:1]23[CH2:8][CH:7]4[CH2:9][CH:3]([CH2:4][CH:5]([CH2:6]4)[CH2:10]2)[CH2:2]3)=[CH:14][C:15]([F:26])=[C:16]([CH:21]=1)[C:17]([O:19][CH3:20])=[O:18])(=[O:25])[CH3:24]

참가 물질

5

반응물 2

HCID 159087TriacetoxyperiodinaneHCID 86703607Methyl 4-(adamantan-1-ylmethoxy)-2-fluoro-5-(1-hydroxyethyl)benzoate

생성물 1

HCID 86703608Methyl 5-acetyl-4-(adamantan-1-ylmethoxy)-2-fluorobenzoate수율 99.1%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 6344Dichloromethane용매2회

실험 절차

To a mixture of methyl 4-(adamantan-1-ylmethoxy)-2-fluoro-5-(1-hydroxyethyl)benzoate (0.76 g, 2.10 mmol) in dichloromethane (20 mL) was added Dess-Martin periodinane (1.34 g, 3.20 mmol). The reaction mixture was stirred for 1 hour at ambient temperature and then quenched by addition of saturated sodium bicarbonate solution (5 mL) and saturated sodium thiosulfate solution (5 mL). Dichloromethane (30 mL) was added and the mixture was stirred for 16 hours at ambient temperature. The organic phase was separated, washed with brine (10 mL), dried over anhydrous sodium sulfate, and filtered. Concentration of the filtrate in vacuo gave a residue, which re-dissolved in a mixture of diethyl ether and dichloromethane (30 mL, 1:1). Insoluble material was filtered off, and the filtrate was concentrated in vacuo to yield the title compound as a colorless oil (0.75 g, 99%): 1H NMR (300 MHz, CDCl3) δ 8.28 (d, J=8.8 Hz, 1H), 6.62 (d, J=12.8 Hz, 1H), 3.78 (s, 3H), 3.55 (s, 2H), 2.55 (s, 3H), 1.97-1.90 (m, 3H), 1.72-1.53 (m, 12H).

후처리

  1. customquenched by addition of saturated sodium bicarbonate solution (5 mL) and saturated sodium thiosulfate solution (5 mL)
  2. additionDichloromethane (30 mL) was added
  3. stirringthe mixture was stirred for 16 hours at ambient temperature
  4. customThe organic phase was separated
  5. washwashed with brine (10 mL)
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. customConcentration of the filtrate in vacuo gave a residue, which
  9. filtrationInsoluble material was filtered off
  10. concentrationthe filtrate was concentrated in vacuo

출처 및 근거

ORD 기록
ord-4433fbf5505846899ff57808e7c0dae2
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08952169B2

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