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

HRID 1109907Notes

Reaction equation

HRID 1109907 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-7b766b4a4bff426b9d1a8895b43975ff
Source dataset
uspto-grants-1994_06
Patent number
US05322953

Reaction notes

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