Sodium Hydroxide → Tributyl-[5-(tetrahydropyran-2-yloxy)-pent-1-ynyl]-stannane

HRID 715960

반응식

HRID 715960 반응식
C([Li])CCC.[CH2:6]([O:11][CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][O:13]1)[CH2:7][CH2:8][C:9]#[CH:10].[CH2:18]([Sn:22](Cl)([CH2:27][CH2:28][CH2:29][CH3:30])[CH2:23][CH2:24][CH2:25][CH3:26])[CH2:19][CH2:20][CH3:21].[OH-].[Na+]>C1COCC1>[CH2:27]([Sn:22]([CH2:18][CH2:19][CH2:20][CH3:21])([CH2:23][CH2:24][CH2:25][CH3:26])[C:10]#[C:9][CH2:8][CH2:7][CH2:6][O:11][CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][O:13]1)[CH2:28][CH2:29][CH3:30]

참가 물질

6

반응물 4

HCID 14798Sodium HydroxideHCID 15096Tributyltin ChlorideHCID 3578162-(4-Pentynyloxy)tetrahydro-2H-pyran2회HCID 178418339Butyllithium

생성물 1

HCID 21579017Tributyl-[5-(tetrahydropyran-2-yloxy)-pent-1-ynyl]-stannane수율 26%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
15 °C

실험 절차

A solution of n-butyllithium (2.5M in hexanes, 22 mL) was added dropwise to a solution of 2-(pent-4-ynyloxy)tetrahydropyran (Intermediate 25, 7.70 g) in THF (60 mL), at −60° C. The mixture was stirred and allowed to warm to 15° C. over 1 hour. It was then re-cooled to −60° C. and a solution of tributyl tin chloride (16.4 g) in THF (50 mL) was added dropwise over 30 minutes. The mixture was stirred and allowed to warm to 20° C. over 1 hour. 1M aqueous sodium hydroxide (4 mL) was cautiously added and the resultant mixture was filtered through Celite, and washed with ethyl acetate. The filtrate was concentrated in vacuo and the residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and cyclohexane with a gradient of 0-100% to give tributyl-[5-(tetrahydropyran-2-yloxy)-pent-1-ynyl]-stannane (5.44 g).

후처리

  1. temperatureIt was then re-cooled to −60° C.
  2. stirringThe mixture was stirred
  3. temperatureto warm to 20° C. over 1 hour
  4. filtrationthe resultant mixture was filtered through Celite
  5. washwashed with ethyl acetate
  6. concentrationThe filtrate was concentrated in vacuo
  7. customthe residue was purified by chromatography on silica
  8. washeluting with a mixture of ethyl acetate and cyclohexane with a gradient of 0-100%

출처 및 근거

ORD 기록
ord-65b835d67c9e4f4a9f460e6d37e31320
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09187494B2

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