Hydrochloric Acid → HCID 59858090、化合物

HRID 254245ノート

反応式

HRID 254245 の反応式
[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

参加物

6

反応物 4

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

生成物 1

HCID 59858090HCID 59858090、化合物

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

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/z 371.2 (M+H+)

後処理

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

出典と根拠

ORDレコード
ord-7f7e4f45a3834aa989a48014be9d9ef7
出典データセット
uspto-grants-2011_01
特許番号
US07875607B2

反応ノート

読み込み中…