5-(Trimethylsilyl)furan-3-carbaldehyde → HCID 19886001, compound

HRID 654967Notes

Reaction equation

HRID 654967 reaction equation
C([Sn]([CH2:14][O:15][CH2:16][O:17][CH2:18][CH2:19][O:20][CH3:21])(CCCC)CCCC)CCC.C([Li])CCC.[CH3:27][Si:28]([CH3:37])([CH3:36])[C:29]1[O:33][CH:32]=[C:31]([CH:34]=[O:35])[CH:30]=1>O1CCCC1>[OH:35][CH:34]([C:31]1[CH:30]=[C:29]([Si:28]([CH3:37])([CH3:36])[CH3:27])[O:33][CH:32]=1)[CH2:14][O:15][CH2:16][O:17][CH2:18][CH2:19][O:20][CH3:21]

Participants

5

Reactant 3

HCID 156632515-(Trimethylsilyl)furan-3-carbaldehydeHCID 15728720HCID 15728720, compoundHCID 178418339Butyllithium

Product 1

HCID 19886001HCID 19886001, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2-methoxyethoxymethyl tributylstannylmethyl ether (620 mg, 1.5 mmole) in tetrahydrofuran (THF) (5 ml) at -78° C. was treated with n-butyl lithium (92.5M solution in hexane: 0.67 ml, 1.67 mmole). After 10 min., a solution of 5-trimethylsilyl-3-furaldehyde (254 mg, 1.5 mmole) in THF (2 ml) was added. The solution was stirred for 3 hours while the cooling bath warmed to room temperature. The mixture was quenched with water and the aqueous phase extracted with ethyl ether. The combined organic portions were dried over MgSO4, filtered and concentrated. Purification by flash chromatography (silica, 50% ethyl ether/hexane) gave 216.5 mg of the title compound as a light yellow oil.

Workup

  1. customThe mixture was quenched with water
  2. extractionthe aqueous phase extracted with ethyl ether
  3. dry with materialThe combined organic portions were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by flash chromatography (silica, 50% ethyl ether/hexane)

Sources & evidence

ORD record
ord-be38337f456a444eaaf7d9e265b8842a
Source dataset
uspto-grants-1992_07
Patent number
US05134128

Reaction notes

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