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3-Benzyloxypropyl 9-(1,3-benzodioxol-5-yl)-8-(benzyloxymethyl)benzo[g][1,3]benzodioxole-7-carboxylate → 3-Hydroxypropyl 9-(1,3-benzodioxol-5-yl)-8-methyl-benzo[g][1,3]benzodioxole-7-carboxylate

HRID 2354594
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인쇄 미리보기

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HRID 2354594 반응식
C([O:8][CH2:9][CH2:10][CH2:11][O:12][C:13]([C:15]1[CH:16]=[C:17]2[C:25](=[C:26]([C:37]3[CH:45]=[CH:44][C:40]4[O:41][CH2:42][O:43][C:39]=4[CH:38]=3)[C:27]=1[CH2:28]OCC1C=CC=CC=1)[C:21]1[O:22][CH2:23][O:24][C:20]=1[CH:19]=[CH:18]2)=[O:14])C1C=CC=CC=1.[H][H]>C1COCC1.[Pd]>[OH:8][CH2:9][CH2:10][CH2:11][O:12][C:13]([C:15]1[CH:16]=[C:17]2[C:25](=[C:26]([C:37]3[CH:45]=[CH:44][C:40]4[O:41][CH2:42][O:43][C:39]=4[CH:38]=3)[C:27]=1[CH3:28])[C:21]1[O:22][CH2:23][O:24][C:20]=1[CH:19]=[CH:18]2)=[O:14]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 2

HCID 52737803-Benzyloxypropyl 9-(1,3-benzodioxol-5-yl)-8-(benzyloxymethyl)benzo[g][1,3]benzodioxole-7-carboxylateHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 52737813-Hydroxypropyl 9-(1,3-benzodioxol-5-yl)-8-methyl-benzo[g][1,3]benzodioxole-7-carboxylate수율 93%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 8028
Tetrahydrofuran
용매

실험 절차

A mixture of 6 (48 mg, 0.079 mmol) and 10% Pd/C (12 mg) in dry THF (5 mL) was stirred for 14 h at room temperature under 1 atm of hydrogen. The mixture was filtered, and the filtrate evaporated at reduced pressure. The residue was purified by column chromatography on silica gel using CH2Cl2/MeOH (40:1, v/v) to yield 7 (30 mg, 93%) as a yellow oil. 1H NMR (CDCl3) δ 8.32 (s, 1H, H4), 7.50 (d, 1H, H5, J=8.7 Hz), 7.18 (d, 1H, H6, J=8.7 Hz), 6.87 (d, 1H, H5′, J=7.8 Hz), 6.72 (d, 1H, H2′, J=1.5 Hz), 6.68 (dd, 1H, H6′, J=1.5, 7.8 Hz), 6.05 (AB, 2H, 3′,4′-OCH2O—, Δδ=9.6 Hz, J=1.5 Hz), 5.83 (AB, 2H, 7,8-OCH2O—, Δδ=1.5 Hz, J=1.5 Hz), 4.54 (t, 2H, 3-COOCH2(CH2)2OH, J=6.3 Hz), 3.83 (t, 2H, 3-COO(CH2)2CH2OH, J=6.3 Hz), 2.34 (s, 3H, 2-CH3), 2.06 (quintet, 2H, 3-COOCH2CH2CH2OH, J=6.3 Hz); MS (EI) m/z 408 [M]+.

후처리

  1. filtrationThe mixture was filtered
  2. customthe filtrate evaporated at reduced pressure
  3. customThe residue was purified by column chromatography on silica gel

출처 및 근거

ORD 기록
ord-97071cbb4ac641668df8871df7214c3f
출처 데이터셋
uspto-grants-2010_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07754718B2

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