Tributylstannane → tert-butyldiphenyl(((5S,6aR)-2,2,6a-trimethyl-tetrahydrofuro[3,2-d][1,3]dioxol-5-yl)methoxy)silane

HRID 409008Notes

Reaction equation

HRID 409008 reaction equation
[C:1]([Si:5]([O:18][CH2:19][C@H:20]1[O:27][CH:26]2[C@:22]([CH3:30])([O:23][C:24]([CH3:29])([CH3:28])[O:25]2)[C@H:21]1I)([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)([CH3:4])([CH3:3])[CH3:2].CCCC[SnH](CCCC)CCCC.CC(N=NC(C#N)(C)C)(C#N)C.[OH-].[Na+]>C1(C)C=CC=CC=1>[C:1]([Si:5]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[O:18][CH2:19][C@H:20]1[O:27][CH:26]2[C@:22]([CH3:30])([O:23][C:24]([CH3:29])([CH3:28])[O:25]2)[CH2:21]1)([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 5948TributylstannaneHCID 6547AzobisisobutyronitrileHCID 14798Sodium HydroxideHCID 66778990tert-butyl(((5R,6S,6aS)-6-iodo-2,2,6a-trimethyl-tetrahydrofuro[3,2-d][1,3]dioxol-5-yl)methoxy)diphenylsilane

Product 1

HCID 66778741tert-butyldiphenyl(((5S,6aR)-2,2,6a-trimethyl-tetrahydrofuro[3,2-d][1,3]dioxol-5-yl)methoxy)silaneYield 86%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of tert-butyl(((5R,6S,6aS)-6-iodo-2,2,6a-trimethyl-tetrahydrofuro[3,2-d][1,3]dioxol-5-yl)methoxy)diphenylsilane (from step 6) (10.3 g, 0.0186 mol), Bu3SnH (5.9 mL, 0.0224 mol) and AIBN (5 mol %) in 120 mL anhydrous toluene was refluxed for 7 h. The reaction mixture was cooled to room temperature and 100 mL of 1N NaOH was added and stirred for one h. This mixture was then finally washed with brine and extracted with ethyl acetate. The organic layers were dried over anhydrous Na2SO4, filtered and concentrated. Purification was performed by column chromatography using hexane and ethyl ether as a gradient mixture to give 6.8 g of viscous title compound in 86% yield.

Workup

  1. washThis mixture was then finally washed with brine
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layers were dried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification

Sources & evidence

ORD record
ord-cb0de1cd426b49838642dd45aa822728
Source dataset
uspto-grants-2014_06
Patent number
US08759318B2

Reaction notes

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