Lithium borohydride → 5-Ethyl-6-(4-hydroxy-3-methyl-but-2-enyl)4-methyl-7-(2-trimethylsilanyl-ethoxy)-3H-isobenzofuran-1-one

HRID 540717노트

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HRID 540717 반응식
[CH2:1]([C:3]1[C:11]([CH3:12])=[C:10]2[C:6]([C:7](=[O:13])[O:8][CH2:9]2)=[C:5]([O:14][CH2:15][CH2:16][Si:17]([CH3:20])([CH3:19])[CH3:18])[C:4]=1[CH2:21][CH:22]=[C:23]([CH3:26])[CH:24]=[O:25])[CH3:2].[BH4-].[Li+]>CO.CO.O.C1COCC1>[CH2:1]([C:3]1[C:11]([CH3:12])=[C:10]2[C:6](=[C:5]([O:14][CH2:15][CH2:16][Si:17]([CH3:18])([CH3:19])[CH3:20])[C:4]=1[CH2:21][CH:22]=[C:23]([CH3:26])[CH2:24][OH:25])[C:7](=[O:13])[O:8][CH2:9]2)[CH3:2]

참가 물질

6

반응물 2

HCID 4148881Lithium borohydrideHCID 725636044-[6-Ethyl-7-methyl-3-oxo-4-(2-trimethylsilanyl-ethoxy)-1,3-dihydro-isobenzofuran-5-yl]-2-methyl-but-2-enal

생성물 1

HCID 670098805-Ethyl-6-(4-hydroxy-3-methyl-but-2-enyl)4-methyl-7-(2-trimethylsilanyl-ethoxy)-3H-isobenzofuran-1-one수율 73.4%

시약·촉매·용매 3

HCID 887Methanol용매HCID 8028Tetrahydrofuran용매HCID 22242641Methanol--water (1/1)용매

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온도
0 °C

실험 절차

4-[6-Ethyl-7-methyl-3-oxo-4-(2-trimethylsilanyl-ethoxy)-1,3-dihydro-isobenzofuran-5-yl]-2-methyl-but-2-enal (77.6 mg, 0.207 mmol) was dissolved in MeOH (4 mL). A solution of CeCl3 (51.1 mg, 0.207 mmol) in MeOH/water (9/1, 0.66 mL) was added and the solution was cooled to 0° C. A solution of lithium borohydride in THF (2M, 0.105 mL) was added dropwise. After 15 minutes, the reaction was quenched with 1N HCl (0.5 mL). The MeOH was removed in vacuo and the crude material was partitioned between DCM and water. The aqueous layer was extracted with DCM and the combined organic layers were washed with sodium bicarbonate solution and dried over sodium sulfate. Filtration and evaporation of solvents yielded a crude oil, which was purified by silica gel chromatography to provide 57.2 mg (73%) of the desired product. 1H NMR (300 MHz, CDCl3): δ=0.04 (s, 9H), 1.15 (t, J=7.8 Hz, 3H), 1.26 (m, 2H), 1.86 (s, 3H), 2.19 (s, 3H), 2.72 (q, J=7.8 Hz, 2H), 3.52 (d, J=6.3 Hz, 2H), 3.99 (s, 2H), 4.34 (m, 2H), 5.14 (s, 2H), 5.32 (m, 1H) ppm.

후처리

  1. customthe reaction was quenched with 1N HCl (0.5 mL)
  2. customThe MeOH was removed in vacuo
  3. customthe crude material was partitioned between DCM and water
  4. extractionThe aqueous layer was extracted with DCM
  5. washthe combined organic layers were washed with sodium bicarbonate solution
  6. dry with materialdried over sodium sulfate
  7. filtrationFiltration and evaporation of solvents
  8. customyielded a crude oil, which
  9. customwas purified by silica gel chromatography

출처 및 근거

ORD 기록
ord-01df3f7f4ef74c87b8e79b0ebcc3cf5d
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08871785B2

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