Decanal → HCID 68811128, compound

HRID 898197Notes

Reaction equation

HRID 898197 reaction equation
C([Li])CCC.Br[C:7]1[CH:14]=[CH:13][C:10]([CH2:11][OH:12])=[CH:9][C:8]=1[CH3:15].[CH:16](=[O:26])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]>O1CCCC1>[OH:26][CH:16]([C:7]1[CH:14]=[CH:13][C:10]([CH2:11][OH:12])=[CH:9][C:8]=1[CH3:15])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]

Participants

5

Reactant 3

HCID 8175DecanalHCID 10987288(4-Bromo-3-methylphenyl)methanolHCID 178418339Butyllithium

Product 1

HCID 68811128HCID 68811128, compoundYield 64.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

n-Butyllithium (2.5 M in hexanes, 8.3 mL, 20.7 mmol) was added dropwise to a solution of 4-bromo-3-methylbenzyl alcohol (1.90 g, 9.44 mmol, from Step A) in tetrahydrofuran (25 mL) at −78° C. After 1 h, n-decanal (2.95 g, 18.89 mmol) was added and the reaction allowed to warm to 0° C. After 30 min, the reaction was quenched with water (25 mL) and diluted with ethyl acetate (25 mL). The organic layer was washed with sat'd sodium chloride (30 mL), dried over magnesium sulfate and concentrated in vacuo. Silica gel chromatography eluting with 25% ethyl acetate/hexane gave 1.69 g (6.07 mmol, 64%) of product: 1H NMR (500 MHz): δ 7.45 (d, J=8.0 Hz, 1H), 7.21 (d, J=7.8 Hz, 1H), 7.14 (s, 1H), 4.88-4.94 (m, 1H), 4.64 (s, 2H), 2.34 (s, 3H), 1.22-1.80 (m, 16H), 0.87 (t, J=7.0 Hz, 3H).

Workup

  1. waitAfter 30 min
  2. customthe reaction was quenched with water (25 mL)
  3. additiondiluted with ethyl acetate (25 mL)
  4. washThe organic layer was washed with sat'd sodium chloride (30 mL)
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. washSilica gel chromatography eluting with 25% ethyl acetate/hexane

Sources & evidence

ORD record
ord-021e693dc36b4df5b5f15850c1e5ecbc
Source dataset
uspto-grants-2008_04
Patent number
US07351725B2

Reaction notes

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