Sodium Chloride → 7,8-Difluoro-2-pentyl-6-[1-(4-propylcyclohexyl)prop-2-ynyloxy]chroman

HRID 1873311ノート

反応式

HRID 1873311 の反応式
[F:1][C:2]1[C:11]([F:12])=[C:10]2[C:5]([CH2:6][CH2:7][CH:8]([CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[O:9]2)=[CH:4][C:3]=1[OH:18].[CH2:19]([CH:22]1[CH2:27][CH2:26][CH:25]([CH:28](O)[C:29]#[CH:30])[CH2:24][CH2:23]1)[CH2:20][CH3:21].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.[Cl-].[Na+]>C1COCC1>[F:1][C:2]1[C:11]([F:12])=[C:10]2[C:5]([CH2:6][CH2:7][CH:8]([CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[O:9]2)=[CH:4][C:3]=1[O:18][CH:19]([CH:22]1[CH2:23][CH2:24][CH:25]([CH2:28][CH2:29][CH3:30])[CH2:26][CH2:27]1)[C:20]#[CH:21]

参加物

7

反応物 5

HCID 5234Sodium ChlorideHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 46834772HCID 46834772、化合物HCID 581519331-(4-Propylcyclohexyl)prop-2-yn-1-ol

生成物 1

HCID 581519077,8-Difluoro-2-pentyl-6-[1-(4-propylcyclohexyl)prop-2-ynyloxy]chroman

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

8.0 g (31.2 mmol) of 7,8-difluoro-2-pentylchroman-6-ol are initially introduced in 75 ml of THF together with 6.75 g (37.4 mmol) of 1-(4-propylcyclohexyl)prop-2-yn-1-ol and 9.83 g (37.6 mmol) of triphenylphosphine, and 7.89 ml (40.6 mmol) of DIAD are added over the course of 30 min with ice-cooling. After 20 h at RT, semi-saturated sodium chloride solution 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 solution, and the solution is dried using sodium sulfate. The residue remaining after removal of the solvents is purified by column chromatography (SiO2, n-pentane:MTBE=2:1), giving 7,8-difluoro-2-pentyl-6-[1-(4-propylcyclohexyl)prop-2-ynyloxy]chroman as a pale-brown oil.

後処理

  1. additionare added over the course of 30 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 solution
  5. customthe solution is dried
  6. customafter removal of the solvents
  7. customis purified by column chromatography (SiO2, n-pentane:MTBE=2:1)

出典と根拠

ORDレコード
ord-ebb990bc988347989bde908591a0fd3b
出典データセット
uspto-grants-2012_11
特許番号
US08303844B2

反応ノート

読み込み中…