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

HRID 1090928Notes

Reaction equation

HRID 1090928 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 1.0M 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. 1HNMR (CDCl3): 0.34 (s, 9H), 0.89 (t, 3H, J=6.9 Hz), 1.26 (br s, 20H), 1.75 (m, 2H), 2.04 (s, 3H), 5.88 (t, 1H, J=7.1 Hz), 6.43 (br s, 1H) and 7.58 (br s, 1H).

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-166ef7269fe04bbcb59a295ab810ef95
Source dataset
uspto-grants-1992_01
Patent number
US05082954

Reaction notes

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