Formaldehyde → 5-(Tert-butyldimethylsilanyloxy)-5-(1-propylcyclobutyl)pent-2-en-1-ol

HRID 2249573Notes

Reaction equation

HRID 2249573 reaction equation
C([Li])(C)(C)C.[C:6]([Si:10]([O:13][CH:14]([C:19]1([CH2:23][CH2:24][CH3:25])[CH2:22][CH2:21][CH2:20]1)[CH2:15][CH:16]=[CH:17]I)([CH3:12])[CH3:11])([CH3:9])([CH3:8])[CH3:7].[CH2:26]=[O:27]>CCCCC.C1COCC1>[Si:10]([O:13][CH:14]([C:19]1([CH2:23][CH2:24][CH3:25])[CH2:22][CH2:21][CH2:20]1)[CH2:15][CH:16]=[CH:17][CH2:26][OH:27])([C:6]([CH3:9])([CH3:8])[CH3:7])([CH3:12])[CH3:11]

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 53961856tert-Butyl-[4-iodo-1-(Propylcyclobutyl)but-3-enyloxy]dimethylsilaneHCID 178418306HCID 178418306, compound

Product 1

HCID 671021205-(Tert-butyldimethylsilanyloxy)-5-(1-propylcyclobutyl)pent-2-en-1-olYield 33%

Reagents, catalysts & solvents 2

HCID 8003PentaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

tert-Butyllithium (1.32 mL of a 1.7M solution in pentane, 2.25 mmol) was added to a solution of the vinyl iodide 6 (460 mg, 1.25 mmol) in THF (2.2 mL) at −78° C. After 0.5 h paraformaldehyde (50 mg, 1.67 mmol) was added. The reaction was warmed to room temperature and stirred for 16 h. The reaction was quenched with saturated aqueous NH4Cl and extracted with EtOAc. The organic portion was dried (MgSO4), filtered and concentrated in vacuo. FCC (silica gel, 4:1 hex/EtOAc) yielded 103 mg (33%) of the alcohol 7 as a clear, colorless oil.

Workup

  1. customThe reaction was quenched with saturated aqueous NH4Cl
  2. extractionextracted with EtOAc
  3. dry with materialThe organic portion was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-daadba8693b64f99a3c95729daec8390
Source dataset
uspto-grants-2008_01
Patent number
US07314890B2

Reaction notes

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