Triphenylphosphine → 7-Ethoxy-1,2-difluoro-3-[1-(4-propylcyclohexyl)prop-2-ynyloxy]naphthalene

HRID 1873324ノート

反応式

HRID 1873324 の反応式
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[CH:10]=[C:9]([OH:14])[C:8]([F:15])=[C:7]2[F:16])[CH3:2].[CH2:17]([CH:20]1[CH2:25][CH2:24][CH:23]([CH:26](O)[C:27]#[CH:28])[CH2:22][CH2:21]1)[CH2:18][CH3:19].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1.O>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]2[C:11]([CH:10]=[C:9]([O:14][CH:17]([CH:20]3[CH2:21][CH2:22][CH:23]([CH2:26][CH2:27][CH3:28])[CH2:24][CH2:25]3)[C:18]#[CH:19])[C:8]([F:15])=[C:7]2[F:16])=[CH:12][CH:13]=1)[CH3:2]

参加物

7

反応物 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 581519196-Ethoxy-3,4-difluoronaphthalen-2-olHCID 581519331-(4-Propylcyclohexyl)prop-2-yn-1-ol

生成物 1

HCID 581518997-Ethoxy-1,2-difluoro-3-[1-(4-propylcyclohexyl)prop-2-ynyloxy]naphthalene

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

10.5 g (46.8 mmol) of 6-ethoxy-3,4-difluoronaphthalen-2-ol are initially introduced in 100 ml of THF together with 10.0 g (55.5 mmol) of 1-(4-propylcyclohexyl)prop-2-yn-1-ol and 15.0 g (57.2 mmol) of triphenylphosphine, and 11.5 ml (59.1 mmol) of DIAD are added over the course of 20 min with ice-cooling. After 18 h at RT, water is added, and the mixture is extracted a number of times with MTBE. The combined organic phases are washed with water and saturated sodium chloride soln., and the solution is dried using sodium sulfate. The residue remaining after removal of the solvents is purified by column chromatography (SiO2, n-heptane:MTBE=2:1). The further purification is carried out by recrystallisation from n-heptane, giving 7-ethoxy-1,2-difluoro-3-[1-(4-propylcyclohexyl)prop-2-ynyloxy]naphthalene as a yellowish solid.

後処理

  1. additionare added over the course of 20 min with ice-
  2. temperaturecooling
  3. extractionthe mixture is extracted a number of times with MTBE
  4. washThe combined organic phases are washed with water and saturated sodium chloride soln
  5. custom, and the solution is dried
  6. customafter removal of the solvents
  7. customis purified by column chromatography (SiO2, n-heptane:MTBE=2:1)
  8. customThe further purification
  9. customis carried out by recrystallisation from n-heptane

出典と根拠

ORDレコード
ord-c0750643218e483cae05a20345c81806
出典データセット
uspto-grants-2012_11
特許番号
US08303844B2

反応ノート

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