Propylethinylcarbinol → 6-(1-Ethynylbutoxy)-7,8-difluoro-2-pentylchroman

HRID 1873313ノート

反応式

HRID 1873313 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].[CH:19]#[C:20][CH:21](O)[CH2:22][CH2:23][CH3:24].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>[C:20]([CH:21]([O:18][C:3]1[CH:4]=[C:5]2[C:10](=[C:11]([F:12])[C:2]=1[F:1])[O:9][CH:8]([CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH2:7][CH2:6]2)[CH2:22][CH2:23][CH3:24])#[CH:19]

参加物

7

反応物 4

HCID 7746PropylethinylcarbinolHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 46834772HCID 46834772、化合物

生成物 1

HCID 581519006-(1-Ethynylbutoxy)-7,8-difluoro-2-pentylchroman

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

10.0 g (39.0 mmol) of 7,8-difluoro-2-pentylchroman-6-ol are initially introduced in 140 ml of THF together with 4.0 g (41.0 mmol) of 1-hexyn-3-ol and 11.3 g (42.9 mmol) of triphenylphosphine, and 9.1 ml (46.8 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), giving 6-(1-ethynylbutoxy)-7,8-difluoro-2-pentylchroman as a yellow oil.

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)

出典と根拠

ORDレコード
ord-2fd8d632df444939aeb159f484faf82f
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…