3-Furancarboxaldehyde, 5-(triethylsilyl)- → 4-(1-Hydroxytridecyl)-2-triethylsilylfuran

HRID 326373Notes

Reaction equation

HRID 326373 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].[CH2:15]([Si:17]([CH2:27][CH3:28])([CH2:25][CH3:26])[C:18]1[O:19][CH:20]=[C:21]([CH:23]=[O:24])[CH:22]=1)[CH3:16]>O1CCCC1>[OH:24][CH:23]([C:21]1[CH:22]=[C:18]([Si:17]([CH2:25][CH3:26])([CH2:15][CH3:16])[CH2:27][CH3:28])[O:19][CH:20]=1)[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 108784383-Furancarboxaldehyde, 5-(triethylsilyl)-HCID 178443215HCID 178443215, compound

Product 1

HCID 156632694-(1-Hydroxytridecyl)-2-triethylsilylfuran

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Dodecylmagnesium bromide (a 1M solution in tetrahydrofuran; 14.3 ml; 14.3 mmol) was added dropwise to a solution of 2-triethylsilyl-4-furaldehyde (2.0 g, 9.52 mmol) in THF (20 ml) at 0 degrees C. under argon. After stirring at room temperature for 2 hours, the mixture was quenched with dilute HCl and extracted with ethyl ether. Evaporation of the dried (magnesium sulfate) extracts gave an oil, which was purified by flash chromatography on silica using 30% ethyl ether/hexane to give the titled alcohol. 1HNMR (CDCl3) 0.76 (q, 6H, J=8.0 Hz), 0.88 (t, 3H, J=6.3 Hz), 0.98 (t, 9H, J=8.0 Hz), 1.25 (m, 20H), 1.62 (d, 1H, J =4.3 Hz), 1.75 (m, 2H), 4.63 (dd, 1H, J=6.6 Hz, 1.9 Hz0, 6.63 (s, 1H) and 7.57 (s, 1H).

Workup

  1. customthe mixture was quenched with dilute HCl
  2. extractionextracted with ethyl ether
  3. customEvaporation of the
  4. dry with materialdried (magnesium sulfate)
  5. customextracts gave an oil, which
  6. customwas purified by flash chromatography on silica using 30% ethyl ether/hexane

Sources & evidence

ORD record
ord-bd8295b6f64e495ea83f5a42d1be1dc1
Source dataset
uspto-grants-1993_12
Patent number
US05268387

Reaction notes

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