Undecanal → Tridec-1-en-3-ol

HRID 1081972

Reaction equation

HRID 1081972 reaction equation
[CH:1]([Mg]Br)=[CH2:2].[CH:5](=[O:16])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15].[Cl-].[NH4+]>O1CCCC1>[CH2:1]=[CH:2][CH:5]([OH:16])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15]

Participants

5

Reactant 3

HCID 8186UndecanalHCID 25517Ammonium ChlorideHCID 178418507HCID 178418507, compound

Product 1

HCID 185797Tridec-1-en-3-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of vinyl magnesium bromide in tetrahydrofuran (1M, 82.0 mL) at 0° C. was added a solution of undecanal i (7.00 g, 41.1 mmol) in tetrahydrofuran (25 mL) in about 10 min. After 6 h at 0° C., saturated ammonium chloride solution (50 mL) was added. The two layers were separated. The water layer was extracted with ether (2×50 mL). The combined organic solutions were dried over anhydrous magnesium sulfate, filtered, and concentrated. The residue was purified by flash chromatography (10% ethyl acetate in hexane) to give 7.94 g (98%) of i-a as a colorless oil: IR (neat) 3409, 3079, 1644, and 1463 cm-1 ; 1H NMR (CDCl3, 300 MHz) δ5.80 (ddd, 1H, J=6.3, 10.7, and 17.2 Hz, CH=CH2), 5.55 (dd, 1H, J=17.2 and 1.4 Hz, CH=CH2), 5.05 (dd, 1H, J=10.7 and 1.4 Hz, CH=CH2), 3.99 (q, 1H, J=6.2 Hz, CHOH), 2.58 (br s, 1H, OH), 1.46-1.22 [m, 18H, C(4-12)H2 ], and 0.83 (t, J=6.4 Hz, CH2CH3); 13C NMR (CDCl3, 75.5 MHz) δ141.61, 114.50, 73.33, 37.24, 32.12, 29.83, 29.55, 25.57, 22.87, and 14.26.

Workup

  1. customThe two layers were separated
  2. extractionThe water layer was extracted with ether (2×50 mL)
  3. dry with materialThe combined organic solutions were dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography (10% ethyl acetate in hexane)
  7. customto give 7.94 g (98%) of i-a as a colorless oil

Sources & evidence

ORD record
ord-8abb01bcb7484fa9a5d660778ad70dcf
Source dataset
uspto-grants-1996_12
Patent number
US05587491

Linked notes

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