Water → HCID 10014874, 화합물

HRID 488156노트

반응식

HRID 488156 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

HCID 10014874HCID 10014874, 화합물수율 92.2%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-7a26416c469e42c98d4859eba10588b6
출처 데이터셋
uspto-grants-1994_03
특허 번호
US05298655

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