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Lithium Chloride → 3-Benzyloxy-5-isobutylbenzoic acid methyl ester

HRID 1430995
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인쇄 미리보기

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HRID 1430995 반응식
[CH3:1][O:2][C:3](=[O:26])[C:4]1[CH:9]=[C:8](OS(C(F)(F)F)(=O)=O)[CH:7]=[C:6]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:5]=1.[Cl-].[Li+].[Br-].[CH2:30]([Zn+])[CH:31]([CH3:33])[CH3:32]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1COCC1>[CH3:1][O:2][C:3](=[O:26])[C:4]1[CH:9]=[C:8]([CH2:30][CH:31]([CH3:33])[CH3:32])[CH:7]=[C:6]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:5]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 433294Lithium ChlorideHCID 18945283Methyl 3-benzyloxy-5-(trifluoromethanesulfonyloxy)benzoateHCID 178448254HCID 178448254, 화합물

생성물 1

HCID 585288613-Benzyloxy-5-isobutylbenzoic acid methyl ester수율 68%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매
HCID 8028
Tetrahydrofuran
용매

실험 절차

To a microwave reaction vial was added 3-benzyloxy-5-trifluoromethanesulfonyloxybenzoic acid methyl ester (70 mg, 0.179 mmol), lithium chloride (23 mg, 0.537 mmol), Pd(PPh3)4 (10 mg, 0.009 mmol) and 3 ml of THF. Isobutylzinc bromide (0.5 M in THF) (0.537 mL, 0.269 mmol) was added and the vial sealed. After heating in microwave reactor at 130° for 5 min the reaction mixture was adsorbed onto silica gel and purified by silica gel chromatography using an ethyl acetate-hexane gradient to afford 36 mg (68%) of 3-benzyloxy-5-isobutylbenzoic acid methyl ester. 1H NMR (300 MHz, DMSO-d6) δ 0.850 (d, 6H, J=6 Hz), 1.78-1.92 (m, 1H), 3.84 (s, 3H), 5.16 (s, 2H), 7.11 (d, 1H, J=2 Hz), 7.33-7.48 (m, 7H).

후처리

  1. customTo a microwave reaction
  2. temperatureAfter heating in microwave reactor at 130° for 5 min the reaction mixture
  3. custompurified by silica gel chromatography

출처 및 근거

ORD 기록
ord-b2464f6e83ef43aa9b5d763b1e907120
출처 데이터셋
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08940927B2

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