2-(Benzyloxy)-5-fluorobenzaldehyde → (+/-)-3-(2-benzyloxy-5-fluoro-phenyl)-3H-isobenzofuran-1-one

HRID 2036235노트

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HRID 2036235 반응식
[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][C:10]=1[CH:11]=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C1COCC1>[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][C:10]=1[CH:11]1[C:7]2[C:2](=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:1](=[O:8])[O:12]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

3

반응물 1

HCID 107281542-(Benzyloxy)-5-fluorobenzaldehyde

생성물 1

HCID 66654413(+/-)-3-(2-benzyloxy-5-fluoro-phenyl)-3H-isobenzofuran-1-one

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

To the Grignard Solution A cooled to −78° C., a solution of 2-benzyloxy-5-fluoro-benzaldehyde (879 mg, 3.82 mmol, 1.0 eq.) in THF (10 mL) was added dropwise. The mixture was stirred at −78° C. for 1 hour and further at r.t. for 18 hours. The reaction was carefully quenched with 1M aq. NH4Cl soln. (50 mL) and AcOEt (100 mL) was added. The resulting suspension was filtered through celite and the filter cake was rinsed with water and AcOEt. The layers were separated and the aq. phase was extracted with AcOEt (2×150 mL). The comb. org. phases were washed with sat. aq. NaCl soln. (1×100 mL), dried over MgSO4, and concentrated in vacuo. The residue was purified by flash master (column: 100 g, flow: 45 mL/min, Heptane to Heptane+45% AcOEt) to yield (±)-3-(2-benzyloxy-5-fluoro-phenyl)-3H-isobenzofuran-1-one as a white solid.

후처리

  1. customThe reaction was carefully quenched with 1M aq. NH4Cl soln
  2. addition(50 mL) and AcOEt (100 mL) was added
  3. filtrationThe resulting suspension was filtered through celite
  4. washthe filter cake was rinsed with water and AcOEt
  5. customThe layers were separated
  6. extractionthe aq. phase was extracted with AcOEt (2×150 mL)
  7. washphases were washed with sat. aq. NaCl soln
  8. dry with material(1×100 mL), dried over MgSO4
  9. concentrationconcentrated in vacuo
  10. customThe residue was purified by flash master (column: 100 g, flow: 45 mL/min, Heptane to Heptane+45% AcOEt)

출처 및 근거

ORD 기록
ord-f7284dfff6dc40c4975be04e66e91ea6
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08575158B2

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