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Potassium Hydroxide → HCID 86755181、化合物

HRID 382451
ノート
印刷プレビュー

反応式

HRID 382451 の反応式
[O:1]1[C@H:3]([CH2:4][CH2:5][CH2:6][CH2:7][CH:8]=[CH2:9])[CH2:2]1.[F:10][C:11]([F:33])([F:32])[O:12][C:13]([F:31])([O:18][C:19]([F:30])([O:24][C:25]([F:29])([F:28])[CH2:26][OH:27])[C:20]([F:23])([F:22])[F:21])[C:14]([F:17])([F:16])[F:15].ClC[C@H](O)CCCCC=C.[OH-].[K+]>O.COCCOC>[F:10][C:11]([F:32])([F:33])[O:12][C:13]([F:31])([O:18][C:19]([F:30])([O:24][C:25]([F:29])([F:28])[CH2:26][O:27][C:8]([CH2:7][CH2:6][CH2:5][CH2:4][CH:3]([OH:1])[CH3:2])=[CH2:9])[C:20]([F:22])([F:21])[F:23])[C:14]([F:17])([F:16])[F:15]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 14797Potassium Hydroxide2 回HCID 6999067(2R)-2-hex-5-enyloxiraneHCID 21967268(R)-8-chloro-7-hydroxy-oct-1-eneHCID 86755182HCID 86755182、化合物2 回

生成物 1

HCID 86755181HCID 86755181、化合物

試薬・触媒・溶媒 2

HCID 962Water
溶媒
HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
45 °C

実験手順

This chlorohydrin was converted in situ to (R)-1,2-epoxy-7-octene and reacted with 2-(2-(2-(trifluoromethoxy(tetrafluoroethoxy)tetrafluoroethoxy)-2,2-difluoroethanol using the following procedure: (R)-8-chloro-7-hydroxy-oct-1-ene (100 g, 0.61 mol), aqueous potassium hydroxide (45 mL of 45 wt. %), 2-(2-(2-(trifluoromethoxy(tetrafluoroethoxy)tetrafluoroethoxy)-2,2-difluoroethanol (291 g, 0.733 mol), Adogen™ 464 (60 g), and 1,2-dimethoxyethane (60 mL) were added to a one liter flask fitted with a mechanical stirrer, an addition funnel, a reflux condenser, and a thermometer. The resulting solution was stirred for one hour at 45° C. and then warmed to 60° C., at which time aqueous potassium hydroxide (70 mL of 45 wt %) was added dropwise. This solution was heated for 2 hours at 60° C. and then at 70° C. for 8 hours. Water (300 mL) was added, and the resulting organic phase was separated and washed with 7 weight % HCl (300 mL). The organic phase was again separated and was concentrated under reduced pressure (25 torr). The resulting crude product was then purified by silica gel chromatography using toluene as eluent to give 268 g of (R)-8-(2-(2-(2-(trifluoromethoxy(tetrafluoroethoxy)tetrafluoroethoxy)-2,2-difluoroethoxy)-7-hydroxyoct-1-ene.

後処理

  1. customfitted with a mechanical stirrer, an addition funnel, a reflux condenser
  2. additionwas added dropwise
  3. temperatureThis solution was heated for 2 hours at 60° C.
  4. waitat 70° C. for 8 hours
  5. customthe resulting organic phase was separated
  6. washwashed with 7 weight % HCl (300 mL)
  7. customThe organic phase was again separated
  8. concentrationwas concentrated under reduced pressure (25 torr)
  9. customThe resulting crude product was then purified by silica gel chromatography

出典と根拠

ORDレコード
ord-2a7f5c26aaf644a9abb729eed8f236fb
出典データセット
uspto-grants-2001_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06309561B1

反応ノート

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