Diethyl Ether → HCID 59330258, 화합물

HRID 1879526노트

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HRID 1879526 반응식
[H-].[CH2:2]([Al+]CC(C)C)C(C)C.[CH3:11][C:12]1[CH:20]=[CH:19][C:18]([CH3:21])=[C:17]2[C:13]=1[CH2:14][O:15][C:16]2=[O:22].C(OCC)C.B(F)(F)F.CCOCC>C1(C)C=CC=CC=1.CO.[Cl-].[Na+].O>[CH3:2][O:22][CH:16]1[C:17]2[C:13](=[C:12]([CH3:11])[CH:20]=[CH:19][C:18]=2[CH3:21])[CH2:14][O:15]1

참가 물질

8

반응물 4

HCID 3283Diethyl EtherHCID 8000Boron trifluoride etherateHCID 5839124,7-Dimethyl-3H-isobenzofuran-1-oneHCID 21225700Diisobutylaluminumhydride

생성물 1

HCID 59330258HCID 59330258, 화합물수율 84%

시약·촉매·용매 3

HCID 887Methanol용매HCID 1140Toluene용매2회HCID 57417360Sodium chloride; water용매

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온도
-50 °C

실험 절차

A 1.0M solution of diisobutylaluminium hydride (115 mL, 0.115 mol) in toluene is added dropwise over a period of 30 mins to a stirred solution of 4,7-dimethyl-3H-isobenzofuran-1-one 4 (18.66 g, 0.115 mol) in anhydrous toluene (250 mL) at −15° C. under nitrogen. Anhydrous diethyl ether (100 mL) is added and the reaction mixture is stirred 4 h at −50° C. The reaction mixture is removed from the cooling bath and diethyl ether (300 mL) is immediately added followed by saturated brine (200 mL). The organic layer is separated and the aqueous layer is re-extracted with diethyl ether (200 mL). The combined organics are dried over sodium sulfate and concentrated in vacuo to yield a cream solid. The solid is dissolved in anhydrous methanol (400 mL) and boron trifluoride diethyl etherate (2.3 mL, 0.018 mol) is added at 0° C. and the solution is stirred for 20 h at RT under nitrogen. The reaction mixture is poured into brine (200 mL) and extracted with petrol 40-60 (2×200 mL). The combined extracts are washed with water (3×100 mL), dried over sodium sulphate, and concentrated in vacuo to yield the product 5 as a yellow oil (17.14 g, 84%): 1H-NMR (300 MHz, CDCl3) δ 7.03 (q, 2H, 3J=7.5 Hz, 4.5 Hz), 6.20 (s, 1H), 5.15 (d, 1H, 3J=13.5 Hz), 4.98 (d, 1H, 3J=13 Hz), 3.42 (s, 3H), 2.31 (s, 3H), 2.20 (s, 3H); 13C-NMR (75 MHz, CDCl3) δ 138.7, 135.3, 130.8, 130.2, 129.1, 128.3, 107.7, 72.2, 54.0, 18.1, 17.5.

후처리

  1. customThe reaction mixture is removed from the cooling bath and diethyl ether (300 mL)
  2. additionis immediately added
  3. customThe organic layer is separated
  4. extractionthe aqueous layer is re-extracted with diethyl ether (200 mL)
  5. dry with materialThe combined organics are dried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customto yield a cream solid
  8. stirringthe solution is stirred for 20 h at RT under nitrogen
  9. extractionextracted with petrol 40-60 (2×200 mL)
  10. washThe combined extracts are washed with water (3×100 mL)
  11. dry with materialdried over sodium sulphate
  12. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-9aaead371688429eaca6a0417e4b7943
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08318048B2

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