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

HRID 715960

反応式

HRID 715960 の反応式
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]

参加物

6

反応物 4

HCID 14798Sodium HydroxideHCID 15096Tributyltin ChlorideHCID 3578162-(4-Pentynyloxy)tetrahydro-2H-pyran2 回HCID 178418339Butyllithium

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
15 °C

実験手順

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).

後処理

  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%

出典と根拠

ORDレコード
ord-65b835d67c9e4f4a9f460e6d37e31320
出典データセット
uspto-grants-2015_11
特許番号
US09187494B2

関連ノート

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