Tributyltin Chloride → HCID 18396100, compound

HRID 609730Notes

Reaction equation

HRID 609730 reaction equation
CC(C)([O-])C.[K+].[Li]CCCC.[CH3:12][O:13][O:14][C@H:15]1[C@H:20]([O:21][O:22][CH3:23])[C@@H:19]([CH2:24][O:25][O:26][CH3:27])[O:18][CH:17]=[CH:16]1.[CH2:28]([Sn:32](Cl)([CH2:37][CH2:38][CH2:39][CH3:40])[CH2:33][CH2:34][CH2:35][CH3:36])[CH2:29][CH2:30][CH3:31]>C1COCC1>[CH2:37]([Sn:32]([CH2:28][CH2:29][CH2:30][CH3:31])([CH2:33][CH2:34][CH2:35][CH3:36])[C:17]1[O:18][C@H:19]([CH2:24][O:25][O:26][CH3:27])[C@@H:20]([O:21][O:22][CH3:23])[C@H:15]([O:14][O:13][CH3:12])[CH:16]=1)[CH2:38][CH2:39][CH3:40]

Participants

6

Reactant 4

HCID 15096Tributyltin ChlorideHCID 23665647Potassium tert-butoxideHCID 54541259HCID 54541259, compoundHCID 178418339Butyllithium

Product 1

HCID 18396100HCID 18396100, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of potassium tert-butoxide (0.42 g, 3.75 mmol) in anhydrous THF (10 mL) was added nBuLi (4.13 mmol) at -78° C. After 15 minutes, tri-O-methoxy-D-glucal (Example 7, 0.194 g, 1.03 mmol) was added in THF (5 mL). After stirring for one hour, tributylstannyl chloride was added and the mixture was allowed to warm to room temperature at which time it was cooled to 0° C. and quenched with ammonium chloride (sat.) and extracted with ethyl acetate three times. The organic layer was washed with water and brine, dried (NaSO4), filtered and concentrated to yield the title compound (0.24 g, 49%) as a clear liquid.

Workup

  1. temperaturewas cooled to 0° C.
  2. customquenched with ammonium chloride (sat.)
  3. extractionextracted with ethyl acetate three times
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried (NaSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-d5c74b093a9f49aabd397fb99ee12ac0
Source dataset
uspto-grants-1999_12
Patent number
US05998438

Reaction notes

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