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

HRID 715960
Notes
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Reaction equation

HRID 715960 reaction equation
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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent
2×

Conditions

Temperature
15 °C

Procedure

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).

Workup

  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%

Sources & evidence

ORD record
ord-65b835d67c9e4f4a9f460e6d37e31320
Source dataset
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09187494B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes