Diethylamine → 2,3-Bis(2R,5R)(2,5-dimethylphospholan-1-yl)-1-benzothiophene

HRID 10771ノート

反応式

HRID 10771 の反応式
[PH2:1][C:2]1[S:6][C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[C:3]=1[PH2:11].[Li]N(CC)CC.N(CC)CC.[Li]CCCC.C[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34].[CH3:35][C@H:36](O)[CH2:37][CH2:38][C@@H:39](O)[CH3:40]>C1COCC1.C(OCC)C.O>[CH3:40][C@@H:39]1[CH2:38][CH2:37][C@@H:36]([CH3:35])[P:1]1[C:2]1[S:6][C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[C:3]=1[P:11]1[C@H:33]([CH3:34])[CH2:32][CH2:31][C@H:30]1[CH3:29]

参加物

9

反応物 5

HCID 8021DiethylamineHCID 69502882,5-Hexanediol, (2S,5S)-HCID 116584572,3-Bisphosphinobenzo[b]thiopheneHCID 178418713HCID 178418713、化合物3 回HCID 178418722HCID 178418722、化合物

生成物 1

HCID 162169732,3-Bis(2R,5R)(2,5-dimethylphospholan-1-yl)-1-benzothiophene収率 53%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒5 回

実験手順

Under argon, a degassed solution of 1.98 g (10 mmol) 2,3-bisphosphinobenzo[b]thiophene in 30 ml THF is treated with 5.5 ml (11 mmol) of a 2N solution of LiNEt2 (freshly prepared from Et2NH and 2.7 M n-BuLi/heptane) in THF. The resulting red solution is added to a degassed solution of the cyclic sulfate derived from (2S,5S)-2,5-hexanediol (3.6 g, 20 mmol) in 40 ml THF at 0° C. The mixture is stirred for 2 h during which time decolorization can be observed. Further 5.5 ml (11 mmol) of a 2N solution of LiNEt2 in THF is added and stirring is continued for 2 h. Then 11 ml (22 mmol) of a 2N solution of LiNEt2 in THF is added. At the end of the addition the mixture becomes more viscous and a precipitate can be observed. After stirring for another 2 h at room temperature 100 ml water and 100 ml diethyl ether are added. The organic layer is removed via double ended needle and the extraction is repeated with 50 ml of diethyl ether. The ether layer is removed as described before, the combined organic layers are dried over sodium sulfate and evaporated yielding 1.91 g (53%) of the title compound as a pale yellow oil.

後処理

  1. stirringstirring
  2. waitis continued for 2 h
  3. additionAt the end of the addition the mixture
  4. additionare added
  5. customThe organic layer is removed
  6. extractionthe extraction
  7. customThe ether layer is removed
  8. dry with materialare dried over sodium sulfate
  9. customevaporated

出典と根拠

ORDレコード
ord-d2db2c76d76647879b5756d327a4ecdc
出典データセット
uspto-grants-2006_08
特許番号
US07094907B2

反応ノート

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