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

HRID 10771노트

반응식

HRID 10771 반응식
[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]

참가 물질

9

반응물 5

HCID 8021DiethylamineHCID 69502882,5-Hexanediol, (2S,5S)-HCID 116584572,3-Bisphosphinobenzo[b]thiopheneHCID 178418713HCID 178418713, 화합물3회HCID 178418722HCID 178418722, 화합물

생성물 1

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

시약·촉매·용매 3

HCID 962Water용매HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매5회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-d2db2c76d76647879b5756d327a4ecdc
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07094907B2

반응 노트

불러오는 중…