4-Methoxybenzyl alcohol → (1-Hydroxy-5-methoxy-3-methyl-naphthalen-2-yl)-(4-methoxy-benzyloxy)-acetic acid ethyl ester

HRID 514037노트

반응식

HRID 514037 반응식
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][OH:8])=[CH:5][CH:4]=1.C[Si]([N-][Si](C)(C)C)(C)C.[K+].[CH2:21]([O:23][C:24](=[O:41])[CH:25]=[C:26]1[CH:35]([CH3:36])[CH:34](Br)[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][C:32]=2[O:38][CH3:39])[C:27]1=[O:40])[CH3:22]>C1COCC1>[CH2:21]([O:23][C:24](=[O:41])[CH:25]([C:26]1[C:35]([CH3:36])=[CH:34][C:33]2[C:28](=[CH:29][CH:30]=[CH:31][C:32]=2[O:38][CH3:39])[C:27]=1[OH:40])[O:8][CH2:7][C:6]1[CH:9]=[CH:10][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)[CH3:22]

참가 물질

5

반응물 3

HCID 77384-Methoxybenzyl alcoholHCID 3251421Potassium bis(trimethylsilyl)amideHCID 86691540(4-bromo-5-methoxy-3-methyl-1-oxo-3,4-dihydro-1H-naphthalen-2-ylidene)-acetic acid ethyl ester

생성물 1

HCID 67126070(1-Hydroxy-5-methoxy-3-methyl-naphthalen-2-yl)-(4-methoxy-benzyloxy)-acetic acid ethyl ester수율 68%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
0 °C

실험 절차

To a solution of 4-methoxybenzyl alcohol (0.27 mL, 4 equiv) in THF (11 mL) at 0° C. was added KHMDS (0.5 M in toluene, 3.4 mL, 3 equiv) and the resulting mixture was allowed to stir for 10 min at 0° C. A solution of (4-bromo-5-methoxy-3-methyl-1-oxo-3,4-dihydro-1H-naphthalen-2-ylidene)-acetic acid ethyl ester (200 mg) in THF (1 mL) was added slowly. After stirring for 3 min at 0° C., the reaction was quenched with citric acid (1 M) and extracted with EtOAc. The organic extracts were washed with brine, dried over Na2SO4 and concentrated. The crude residue was purified by flash column chromatography (5-20% EtOAc/hexanes) to give 157 mg of pale orange oil (68% yield). LCMS-ESI+ (m/z): [M+H]+ calcd for C24H27O6: 411.18. Found: 411.21.

후처리

  1. stirringAfter stirring for 3 min at 0° C.
  2. customthe reaction was quenched with citric acid (1 M)
  3. extractionextracted with EtOAc
  4. washThe organic extracts were washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customThe crude residue was purified by flash column chromatography (5-20% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-903d7234fedb4984bb35bce9ab864c09
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09102614B2

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