Sodium hydride → 5-Ethyl-4-(2-methoxy-ethoxymethoxy)-2-methyl-benzaldehyde
Reaction equation
[CH2:1]([C:3]1[C:4]([OH:12])=[CH:5][C:6]([CH3:11])=[C:7]([CH:10]=1)[CH:8]=[O:9])[CH3:2].[H-].[Na+].[CH3:15][O:16][CH2:17][CH2:18][O:19][CH2:20]Cl>C1COCC1>[CH2:1]([C:3]1[C:4]([O:12][CH2:15][O:16][CH2:17][CH2:18][O:19][CH3:20])=[CH:5][C:6]([CH3:11])=[C:7]([CH:10]=1)[CH:8]=[O:9])[CH3:2]Participants
Procedure
A solution of 5-ethyl-4-hydroxy-2-methyl-benzaldehyde (0.9 g, 5.5 mmol) dissolved in THF (10 mL) was added to a cooled 0° C. suspension of NaH (0.29 g, 7.2 mmol, 60% dispersion in mineral oil) in THF (5 ml). After the addition was complete the reaction mixture was warmed up to room temperature and stirred for 30 mins. 2-Methoxyethoxymethyl chloride (0.82 mL, 7.1 mmol) was added and the reaction was stirred for 4 hours. The reaction mixture was quenched with 1N HCl and extracted with EtOAc. The organic layers were washed with brine, dried over Na2SO4 and concentrated to a yellow oil. Purification by flash column chromatography (10% to 20% EtOAc in hexanes) gave the title compound as a clear oil (0.89 g, 65%). 1H NMR (400 MHz, CDCl3): δ 1.21 (t, J=7.3 Hz, 3 H), 2.63 (m, 5 H), 3.39 (s, 3 H), 3.57 (m, 2 H), 3.84 (m, 2 H), 5.37 (s, 2 H), 6.95 (s, 1 H), 7.62 (s, 1 H), 10.15 (s, 1 H).
Workup
- additionwas added to a cooled 0° C.
- additionAfter the addition
- stirringthe reaction was stirred for 4 hours
- customThe reaction mixture was quenched with 1N HCl
- extractionextracted with EtOAc
- washThe organic layers were washed with brine
- dry with materialdried over Na2SO4
- concentrationconcentrated to a yellow oil
- customPurification by flash column chromatography (10% to 20% EtOAc in hexanes)
Sources & evidence
- ORD record
- ord-4fec192e9b0a461eae56476a818c5b8a
- Source dataset
- uspto-grants-2006_12
- Patent number
- US07148226B2
Reaction notes
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