Acetic Anhydride → 3-(1-Acetoxytridecyl)-2-trimethylsilylfuran

HRID 1109908Notes

Reaction equation

HRID 1109908 reaction equation
[CH2:1]([Mg]Br)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[CH3:15][Si:16]([CH3:25])([CH3:24])[C:17]1[O:18][CH:19]=[CH:20][C:21]=1[CH:22]=[O:23].[C:26](OC(=O)C)(=[O:28])[CH3:27]>O1CCCC1>[C:26]([O:23][CH:22]([C:21]1[CH:20]=[CH:19][O:18][C:17]=1[Si:16]([CH3:25])([CH3:24])[CH3:15])[CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])(=[O:28])[CH3:27]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 150371652-(Trimethylsilyl)furan-3-carbaldehydeHCID 178443215HCID 178443215, compound

Product 1

HCID 150371423-(1-Acetoxytridecyl)-2-trimethylsilylfuran

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Dodecylmagnesium bromide (a 1.0 M solution in tetrahydrofuran; 14.3 ml; 14.3 mmol) was added to a solution 2-trimethylsilyl-3-furaldehyde (1.20 g, 7.1 mmol) in tetrahydrofuran (20 ml). When all the aldehyde was consumed, as monitored by tlc, acetic anhydride (2.02 ml, 21.4 mmol) was added. Stirring was continued at room temperature for 14 hours. The mixture was quenched with water and was extracted with ethyl ether. Evaporation of the dried (magnesium sulfate) extracts gave an oil, which was purified by a silica column using 2% ethyl ether/hexane to give the titled furan.

Workup

  1. customWhen all the aldehyde was consumed
  2. additionwas added
  3. customThe mixture was quenched with water
  4. extractionwas extracted with ethyl ether
  5. customEvaporation of the
  6. dry with materialdried (magnesium sulfate)
  7. customextracts gave an oil, which
  8. customwas purified by a silica column

Sources & evidence

ORD record
ord-d884a8e7e4c64a928bdea6a6e9cd76ba
Source dataset
uspto-grants-1994_06
Patent number
US05322953

Reaction notes

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