Water → tributyl(3,4-dihydro-2H-pyran-6-yl)stannane

HRID 1696278Notes

Reaction equation

HRID 1696278 reaction equation
[O:1]1[CH:6]=[CH:5][CH2:4][CH2:3][CH2:2]1.C([Li])(C)(C)C.[CH2:12]([Sn:16](Cl)([CH2:21][CH2:22][CH2:23][CH3:24])[CH2:17][CH2:18][CH2:19][CH3:20])[CH2:13][CH2:14][CH3:15].O>C1COCC1>[CH2:21]([Sn:16]([CH2:12][CH2:13][CH2:14][CH3:15])([CH2:17][CH2:18][CH2:19][CH3:20])[C:6]1[O:1][CH2:2][CH2:3][CH2:4][CH:5]=1)[CH2:22][CH2:23][CH3:24]

Participants

6

Reactant 4

HCID 962WaterHCID 80803,4-dihydro-2H-pyranHCID 15096Tributyltin ChlorideHCID 178418306HCID 178418306, compound

Product 1

HCID 4216837tributyl(3,4-dihydro-2H-pyran-6-yl)stannane

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

A mixture of 3,4-dihydro-2H-pyran (500 mg, 5.94 mmol) in THF (10 mL) was brought to −78° C. followed by the addition of tert-butyllithium (12.2 mL, 20.8 mmol, 1.7 M in pentane). The resulting yellow solution was brought to 0° C. and stirred for 15 min. The reaction was then cooled to −78° C. and tributyltin chloride (4.8 mL, 17.8 mmol) was slowly added. The reaction was monitored by TLC. Upon completion by TLC, water was added (20 mL) to the reaction. The organic phase was separated, washed with water, dried over MgSO4, concentrated and chromatographed on silica gel using hexanes (500 ml hexanes and 0.5 mL triethylamine). The title compound was obtained as a colorless oil. MS m/z: 375 (M+1).

Workup

  1. customwas brought to −78° C.
  2. customwas brought to 0° C.
  3. customto the reaction
  4. customThe organic phase was separated
  5. washwashed with water
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated
  8. customchromatographed on silica gel

Sources & evidence

ORD record
ord-cd3e81e1d9654e63bb4f84cffa82e538
Source dataset
uspto-grants-2012_04
Patent number
US08163766B2

Reaction notes

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