Acetic Anhydride → HCID 19885938, compound

HRID 654968Notes

Reaction equation

HRID 654968 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.[C:38](OC(=O)C)(=[O:40])[CH3:39]>O1CCCC1.CCCCCC>[C:38]([O: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])(=[O:40])[CH3:39]

Participants

7

Reactant 4

HCID 7918Acetic AnhydrideHCID 156632515-(Trimethylsilyl)furan-3-carbaldehydeHCID 15728720HCID 15728720, compoundHCID 178418339Butyllithium

Product 1

HCID 19885938HCID 19885938, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

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 (a 2.5M 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. Acetic anhydride (309 mg, 3.03 mmole) was added and the solution stirred at room temperature overnight. 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 the title compound as a light yellow oil.

Workup

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

Sources & evidence

ORD record
ord-eb6a66dd789f48f9bd0f521e7a68aeca
Source dataset
uspto-grants-1992_07
Patent number
US05134128

Reaction notes

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