3-Furancarboxaldehyde, 5-(triethylsilyl)- → 4-(1-Hydroxytridecyl)-2-triethylsilylfuran

HRID 273965

반응식

HRID 273965 반응식
[CH2:1]([Mg]Br)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[CH2:15]([Si:17]([CH2:27][CH3:28])([CH2:25][CH3:26])[C:18]1[O:19][CH:20]=[C:21]([CH:23]=[O:24])[CH:22]=1)[CH3:16]>O1CCCC1>[OH:24][CH:23]([C:21]1[CH:22]=[C:18]([Si:17]([CH2:25][CH3:26])([CH2:15][CH3:16])[CH2:27][CH3:28])[O:19][CH:20]=1)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1]

참가 물질

4

반응물 2

HCID 108784383-Furancarboxaldehyde, 5-(triethylsilyl)-HCID 178443215HCID 178443215, 화합물

생성물 1

HCID 156632694-(1-Hydroxytridecyl)-2-triethylsilylfuran

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

Dodecylmagnesium bromide (a 1M solution in tetrahydrofuran; 14.3 ml; 14.3 mmol) was added dropwise to a solution of 2-triethylsilyl-4-furaldehyde (2.0 g, 9.52 mmol) in THF (20 ml) at 0 degrees C. under argon. After stirring at room temperature for 2 hours, the mixture was quenched with dilute HCl and extracted with ethyl ether. Evaporation of the dried (magnesium sulfate) extracts gave an oil, which was purified by flash chromatography on silica using 30% ethyl ether/hexane to give the titled alcohol. 1HNMR (CDCl3) 0.76 (q, 6H, J=8.0 Hz), 0.88 (t, 3H, J=6.3 Hz), 0.98 (t, 9H, J=8.0 Hz), 1.25 (m, 20H), 1.62 (d, 1H, J=4.3 Hz), 1.75 (m, 2H), 4.63 (dd, 1H, J=6.6 Hz, 1.9 Hz), 6.63 (s, 1H) and 7.57 (s, 1H).

후처리

  1. customthe mixture was quenched with dilute HCl
  2. extractionextracted with ethyl ether
  3. customEvaporation of the
  4. dry with materialdried (magnesium sulfate)
  5. customextracts gave an oil, which
  6. customwas purified by flash chromatography on silica using 30% ethyl ether/hexane

출처 및 근거

ORD 기록
ord-66d9dbc2c7164687bd1e6c500e1c2450
출처 데이터셋
uspto-grants-1995_02
특허 번호
US05387606

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