2-Chloroethanol → (2-Chloroethoxy)-adamantylideneadamantane

HRID 247155

反応式

HRID 247155 の反応式
Br[C:2]12[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:10][CH:4]([CH2:5]3)[C:3]1=[C:12]1[CH:19]3[CH2:20][CH:15]4[CH2:16][CH:17]([CH2:21][CH:13]1[CH2:14]4)[CH2:18]3)[CH2:9]2.[Cl:22][CH2:23][CH2:24][OH:25]>O1CCOCC1>[Cl:22][CH2:23][CH2:24][O:25][C:2]12[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:10][CH:4]([CH2:5]3)[C:3]1=[C:12]1[CH:19]3[CH2:20][CH:15]4[CH2:16][CH:17]([CH2:21][CH:13]1[CH2:14]4)[CH2:18]3)[CH2:9]2

参加物

4

反応物 2

HCID 342-ChloroethanolHCID 70517409Bromoadamantylideneadamantane

生成物 1

HCID 86741866(2-Chloroethoxy)-adamantylideneadamantane収率 89.7%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

The bromo-substituted compound having formula 16 (220 mg, 0.58 mmol) was dissolved in dry dioxane (10 cm3) and 2-chloroethanol (5 cm3) was added. The mixture was refluxed for 18 hours, cooled, and concentrated at a reduced pressure. Water (50 cm3) was added and the product was twice extracted with n-hexane, with the combined extracts being washed with brine. The hexane solution was dried with MgSO4, filtered and concentrated at a reduced pressure. Columnchromatography over Al2O3 (act. II/III), using hexane as the eluent, produced 180 mg (0.52 mmol, 89.7%) of pure compound having formula 23 in the form of a colourless oil. IR (neat) 2950 (s), 1455 (m), 1100 (s) and 785 cm-1 (s) 1H-NMR (CCl4, TMS): δ 3.6 (double triplet, 4H), 3.25 (m, 1H), 2.85 (m, 5H), δ 2.4-1.1 (m, 22H), 13C-NMR (CBCl3): δ 135.8; 130.8; 82.6 (d); 67.9 (t); 43.2 (t); 39.7; 39.6; 39.5; 39.1; 37.1; 36.8; 35.7; 33.0; 32.4; 32.1; 31.8; 31.0; 30.1; 28.4 and 27.6. Mass: M+ at m/e 346 (100%). Exact mass: calculated for C22H31ClO: 346.206. Found 346.205.

後処理

  1. temperatureThe mixture was refluxed for 18 hours
  2. temperaturecooled
  3. concentrationconcentrated at a reduced pressure
  4. additionWater (50 cm3) was added
  5. extractionthe product was twice extracted with n-hexane, with the combined extracts
  6. washbeing washed with brine
  7. dry with materialThe hexane solution was dried with MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated at a reduced pressure

出典と根拠

ORDレコード
ord-2c0bc07685db4affbbd8907fe101a7bf
出典データセット
uspto-grants-1987_11
特許番号
US04705847

関連ノート

読み込み中…