Acetaldehyde → HCID 178492627, compound

HRID 1490144Notes

Reaction equation

HRID 1490144 reaction equation
[CH3:1][O:2][C:3]1[CH:15]=[CH:14][C:6]([O:7][C@H:8]2[CH2:11][C@H:10]([C:12]#[CH:13])[CH2:9]2)=[CH:5][CH:4]=1.C([Li])CCC.[CH:21](=[O:23])[CH3:22]>C1COCC1>[CH3:1][O:2][C:3]1[CH:15]=[CH:14][C:6]([O:7][C@H:8]2[CH2:9][C@H:10]([C:12]#[C:13][CH:21]([OH:23])[CH3:22])[CH2:11]2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 177AcetaldehydeHCID 178418339ButyllithiumHCID 178455821HCID 178455821, compound

Product 1

HCID 178492627HCID 178492627, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-40 °C

Procedure

A solution of {trans-3-(4-methoxyphenoxy)cyclobutyl }ethyne (6.40 g, 32.0 mmol) in THF (80 ml) at -78° C. under argon atmosphere was added n-butyllithium (23.7 ml, 38.0 mmol). The mixture was stirred for 0.5 h at the same temperature and then allowed to warm to -40° C. over 1 h. The mixture was recooled to -78° C., a solution of dry acetaldehyde (3.52 g, 80.0 mmol) in THF (20 ml) added to the mixture and the whole stirred overnight at room temperature. The reaction was quenched with saturated aqueous ammonium chloride solution (100 ml) and the whole extracted with ethyl acetate (200 ml). The combined extracts were washed with brine (200 ml), dried (MgSO4) and concentrated in vacuo. Purification by column chromatography {SiO2, 500 g; hexane/ethyl acetate (3/1)} afforded 7.58 g (97%) of 4-{trans-3-(4-methoxyphenoxy)cyclobutyl }-3-butyn-2-ol as white solids: 1H NMR δ6.85-6.68 (m, 4H), 4.89-4.78 (m, 1H), 4.62-4.50 (m, 1H), 3.76 (s, 3H), 3.22-3.09 (m, 1H), 2.59-2.40 (m, 4H), 1.65 (s, 1H), 1.45 (d, J=6.9 Hz, 3H).

Workup

  1. customwas recooled to -78° C.
  2. stirringthe whole stirred overnight at room temperature
  3. customThe reaction was quenched with saturated aqueous ammonium chloride solution (100 ml)
  4. extractionthe whole extracted with ethyl acetate (200 ml)
  5. washThe combined extracts were washed with brine (200 ml)
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customPurification by column chromatography {SiO2, 500 g

Sources & evidence

ORD record
ord-5249c3e2c48947f3a4c2ca6a5cb447c6
Source dataset
uspto-grants-1997_10
Patent number
US05681858

Reaction notes

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