Water → 3-(7-Isobutyl-1-methylazulen-4-yl)butyl 3-butenecarboxylate

HRID 2368

反応式

HRID 2368 の反応式
[C:1](Cl)(=[O:5])/[CH:2]=[CH:3]/[CH3:4].[CH2:7]([C:11]1[CH:20]=[C:19]2[C:15](=[CH:16][CH:17]=[C:18]2[CH3:21])[C:14]([CH:22]([CH3:26])[CH2:23][CH2:24][OH:25])=[CH:13][CH:12]=1)[CH:8]([CH3:10])[CH3:9].[CH2:27](N(CC)CC)C.O>O1CCCC1>[CH2:2]([C:1]([O:25][CH2:24][CH2:23][CH:22]([C:14]1[C:15]2[C:19](=[CH:20][C:11]([CH2:7][CH:8]([CH3:10])[CH3:9])=[CH:12][CH:13]=1)[C:18]([CH3:21])=[CH:17][CH:16]=2)[CH3:26])=[O:5])[CH2:3][CH:4]=[CH2:27]

参加物

6

反応物 4

HCID 962WaterHCID 8471TriethylamineHCID 643131trans-Crotonyl chlorideHCID 196903133-(7-Isobutyl-1-methylazulen-4-yl)butanol

生成物 1

HCID 196903163-(7-Isobutyl-1-methylazulen-4-yl)butyl 3-butenecarboxylate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

10.0 g (0.07 mol) of crotonyl chloride were added dropwise at room temperature to a solution of 7.26 g (0.03 mol) of 3-(7-isobutyl-1-methylazulen-4-yl)butanol and 30 ml of triethylamine in 100 ml of tetrahydrofuran, and the mixture was stirred for 2 hours. 50 ml of water were then added, and the batch was thoroughly stirred. It was then extracted with methyl t-butyl ether, the extract was dried over sodium sulfate, the solvent was evaporated off, and the residue remaining behind was chromatographed over silica gel (9:1 v/v petroleum ether/ethyl acetate). This gave 8.2 g (88%) of a product, which was uniform according to GC, as a highly viscous blue oil. Physical data: IR (KBr): 2959, 2927 (CH); 1738 (C=O); 1464, 1423, 1388, 1327, 1256, 1173, 921 cm-1. 1H-NMR (CDCl3): δ=1.47 (d, 6H); 2.18 (cm, 2H); 2.65 (s, 3H); 3.08 (m, 3H), 3.20 (t, 2H); 4.18 (t, 2H); 5.18 (m, 2H); 5.94 (m, 1H); 6.95 (d, 1H); 7.28 (bs, 1H); 7.40 (d, 1H); 7.62 (bs, 1H); 8.18 (s, 1H) ppm. 13C-NMR (CDCl3): δ=12.84; 24.71 (2C); 30.18; 34.50; 38.28; 39.23; 64.41; 112.33; 118.36; 124.39; 125.47; 130.49; 133.28; 135.10; 136.42; 136.60; 137.31; 140.04; 147.49; 171.29 ppm. MS: m/e=310.4 (C21H28O2+, 80%)

後処理

  1. stirringthe batch was thoroughly stirred
  2. extractionIt was then extracted with methyl t-butyl ether
  3. dry with materialthe extract was dried over sodium sulfate
  4. customthe solvent was evaporated off
  5. customthe residue remaining behind was chromatographed over silica gel (9:1 v/v petroleum ether/ethyl acetate)

出典と根拠

ORDレコード
ord-f7d58edbb5e54cc089f19cc68f88af86
出典データセット
uspto-grants-1998_03
特許番号
US05728867

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