2-(Trimethylsilyl)furan-3-carbaldehyde → 3-(1-Hydroxytridecyl)-2-trimethylsilylfuran

HRID 1681537Notes

Reaction equation

HRID 1681537 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]>O1CCCC1>[OH:23][CH:22]([C:21]1[CH:20]=[CH:19][O:18][C:17]=1[Si:16]([CH3:25])([CH3:24])[CH3:15])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1]

Participants

4

Reactant 2

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

Product 1

HCID 150371683-(1-Hydroxytridecyl)-2-trimethylsilylfuran

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of dodecylmagnesium bromide (a 1M solution in tetrahydrofuran; 14.3 ml; 14.3 mmol) was added to a solution of 2-trimethylsilyl-3-furaldehyde (1.20 g, 7.1 mmol) in tetrahydrofuran (30 ml) at 0°. After all the aldehyde has reacted, as shown by tlc, the mixture was quenched with dilute hydrochloric acid and was extracted with ethyl ether. Evaporation of the dried (magnesium sulfate) extracts gave an oil, which was purified by a silica column using 5% ethyl ether/hexane to give the title furan.

Workup

  1. customthe mixture was quenched with dilute hydrochloric acid
  2. extractionwas extracted with ethyl ether
  3. customEvaporation of the
  4. dry with materialdried (magnesium sulfate)
  5. customextracts gave an oil, which
  6. customwas purified by a silica column

Sources & evidence

ORD record
ord-cad8c6a7f04a490ba919928b18856aba
Source dataset
uspto-grants-1992_12
Patent number
US05171863

Reaction notes

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