Tetrahydrofuran → (S)-ethyl 2-tert-butoxy-2-(6-formyl-3-methyl-1-(trifluoromethyl-sulfonyloxy)naphthalen-2-yl)acetate

HRID 926180노트

반응식

HRID 926180 반응식
[C:1]([O:5][C@@H:6]([C:12]1[C:21]([CH3:22])=[CH:20][C:19]2[C:14](=[CH:15][CH:16]=[C:17]([CH:23]=C)[CH:18]=2)[C:13]=1[O:25][S:26]([C:29]([F:32])([F:31])[F:30])(=[O:28])=[O:27])[C:7]([O:9][CH2:10][CH3:11])=[O:8])([CH3:4])([CH3:3])[CH3:2].C1C[O:36]CC1>O>[C:1]([O:5][C@@H:6]([C:12]1[C:21]([CH3:22])=[CH:20][C:19]2[C:14](=[CH:15][CH:16]=[C:17]([CH:23]=[O:36])[CH:18]=2)[C:13]=1[O:25][S:26]([C:29]([F:32])([F:30])[F:31])(=[O:27])=[O:28])[C:7]([O:9][CH2:10][CH3:11])=[O:8])([CH3:2])([CH3:3])[CH3:4]

참가 물질

4

반응물 2

HCID 8028TetrahydrofuranHCID 89733247(S)-ethyl 2-tert-butoxy-2-(3-methyl-1-(trifluoromethylsulfonyloxy)-6-vinylnaphthalen-2-yl)acetate

생성물 1

HCID 88583821(S)-ethyl 2-tert-butoxy-2-(6-formyl-3-methyl-1-(trifluoromethyl-sulfonyloxy)naphthalen-2-yl)acetate

시약·촉매·용매 1

HCID 962Water용매

실험 절차

A solution of (S)-ethyl 2-tert-butoxy-2-(3-methyl-1-(trifluoromethylsulfonyloxy)-6-vinylnaphthalen-2-yl)acetate (0.60 g, 1.3 mmol) in THF (7 mL) at room temperaturewas treated with a previously prepared mixture of K2OsO4.2H2O (0.023 g, 0.063 mmol) and NaIO4 (0.81 g, 3.8 mmol) in water (5 mL). The resulting suspension becomes thick and opaque. After vigorous stirring for 20 min, the suspension is filtered through a pad of Celite, and the filtrate is washed with batches of EtOAc until white in color. The collected mother liquor is further diluted with water and EtOAc. Following separation, the aqueous layer is extracted with EtOAc until colorless. The combined organics are washed with brine, dried over anhydrous MgSO4, filtered and concentrated in vacuo. The residue is purified by Yamazen column chromatography (15-35% EtOAc/hex) to afford the desired material. 1H-NMR: 400 MHz, (CDCl3) δ: 10.19 (s, 1H); 8.31 (br s, 1H); 8.16 (d, J=8.8 Hz, 1H); 8.05 (dd, J=8.8, 1.6 Hz, 1H); 7.85 (s, 1H); 5.76 (s, 1H); 4.28-4.10 (m, 2H); 2.61 (s, 3H); 1.22 (s, 9H); 1.18 (t, J=7.2 Hz, 3H).

후처리

  1. filtrationthe suspension is filtered through a pad of Celite
  2. washthe filtrate is washed with batches of EtOAc until white in color
  3. additionThe collected mother liquor is further diluted with water and EtOAc
  4. customseparation
  5. extractionthe aqueous layer is extracted with EtOAc until colorless
  6. washThe combined organics are washed with brine
  7. dry with materialdried over anhydrous MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe residue is purified by Yamazen column chromatography (15-35% EtOAc/hex)

출처 및 근거

ORD 기록
ord-5fa6417698944799af558c716835d425
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09284323B2

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