Hydrochloric Acid → HCID 59858090, 화합물

HRID 2378378노트

반응식

HRID 2378378 반응식
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]3[CH:15]4[CH2:16][CH:12]([CH2:13][CH2:14]4)[C:11]=13)[O:8][C:7]([CH2:18][CH2:19][C:20]([OH:22])=[O:21])([CH3:17])[CH2:6][CH2:5]2.[OH-].[Na+].[CH2:25](Br)[CH:26]=[C:27]([CH3:29])[CH3:28].Cl>CCOC(C)=O>[OH:1][C:2]1[C:3]([CH2:25][CH:26]=[C:27]([CH3:29])[CH3:28])=[C:4]2[C:9](=[C:10]3[CH:15]4[CH2:16][CH:12]([CH2:13][CH2:14]4)[C:11]=13)[O:8][C:7]([CH2:18][CH2:19][C:20]([OH:22])=[O:21])([CH3:17])[CH2:6][CH2:5]2

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 700922-Butene, 1-bromo-3-methyl-HCID 11609154HCID 11609154, 화합물

생성물 1

HCID 59858090HCID 59858090, 화합물

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

A solution of 3-(6-hydroxy-2-methyl-3,4,7,8,9,10-hexahydro-7,10-methano-2H-benzo[h]chromen-2-yl)-propionic acid, (2.39 mmol) in 1M aq. NaOH (4.8 mL, 4.8 mmol) was cooled to 0° C., and treated with prenyl bromide (0.277 mL, 2.39 mmol). Following stirring for 7 h at ambient temperature the reaction mixture was made slightly acidic with 0.5M HCl and shaken with EtOAc. The organic phase was evaporated yielding 1. The mixture was subjected to column chromatography on silica gel (SiO2: hexane:EtOAc, 85:15 v/v eluting yielded 3-[6-hydroxy-2-methyl-5-(3-methyl-but-2-enyl)-3,4,7,8,9,10-hexahydro-7,10-methano-2H-benzo[h]chromen-2-yl]-propionic acid 1H-NMR (300 MHz, CDCl3) δ (ppm): 5.17 (t, J=6, 1H), 3.54 (br s, 1H), 3.49 (br s, 1H), 3.18-3.37 (m, 2H), 2.70 (t, J=7, 2H), 2.49-2.62 (m, 2H), 1.60-2.07 (m, 13H), 1.39-1.48 (m, 1H), 1.05-1.32 (m, 5H). 13C-NMR (75 MHz CDCl3) δ (ppm): 180.1, 141.1, 133.9, 133.3, 132.9, 122.9, 122.3, 117.4, 73.2, 49.0, 48.9, 40.0, 39.8, 33.6, 32.0, 28.7, 26.7, 25.9, 25.6, 23.8, 233.2, 20.5, 18.0. MS ESI-Pos m/z371.2 (M+H+)

후처리

  1. customThe organic phase was evaporated
  2. customyielding 1
  3. washhexane:EtOAc, 85:15 v/v eluting

출처 및 근거

ORD 기록
ord-64c69d1a2b434ae2953e247ee80174cb
출처 데이터셋
uspto-grants-2008_12
특허 번호
US07470798B2

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