Water → HCID 10014874、化合物

HRID 488156ノート

反応式

HRID 488156 の反応式
[CH3:1]/[C:2](/[CH2:6][CH2:7]/[CH:8]=[C:9](\[CH3:16])/[CH2:10][CH2:11][CH:12]=[C:13]([CH3:15])[CH3:14])=[CH:3]\[CH2:4]Br.[N-:17]=[N+:18]=[N-:19].[Na+].O>CN(C=O)C>[CH3:1]/[C:2](/[CH2:6][CH2:7]/[CH:8]=[C:9](\[CH3:16])/[CH2:10][CH2:11][CH:12]=[C:13]([CH3:15])[CH3:14])=[CH:3]\[CH2:4][N:17]=[N+:18]=[N-:19]

参加物

5

反応物 3

HCID 962WaterHCID 33557Sodium AzideHCID 5366048(2E,6E)-1-bromo-3,7,11-trimethyldodeca-2,6,10-triene

生成物 1

HCID 10014874HCID 10014874、化合物収率 92.2%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A mixture of (E,E)-3,7,11-trimethyl-2,6,10-dodecatrienyl bromide (1.5 g, 5.26 mmol) and sodium azide (0.68 g, 10.5 mmol) in DMF (20 mL) was stirred at room temperature for 0.5 hours, then poured into cold water and extracted with ether. The ethereal extract was washed with brine, dried, filtered and evaporated to yield a residue. Purification of the residue by flash chromatography on a silica gel column, using hexane as the eluant, afforded the title compound as an oil (1.2 g, 4.85 mmol, 92%) NMR (CDCl3): δ5.35 (H, t, J=7Hz), 5.10 (2H, m), 3.78 (2H, d, J=7Hz), 1.9-2.2 (8H, m), 1.72 (3H, s), 1.68 (3H, s) 1.60 (6H, s).

後処理

  1. extractionextracted with ether
  2. extractionThe ethereal extract
  3. washwas washed with brine
  4. customdried
  5. filtrationfiltered
  6. customevaporated
  7. customto yield a residue
  8. customPurification of the residue by flash chromatography on a silica gel column

出典と根拠

ORDレコード
ord-7a26416c469e42c98d4859eba10588b6
出典データセット
uspto-grants-1994_03
特許番号
US05298655

反応ノート

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