Tetrahydrofuran → (2S)-2-[(5-methylindolyl)methyl]pent-4-en-1-ol

HRID 498983Notes

Reaction equation

HRID 498983 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH3:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][C:12]([CH2:17][CH2:18][C:19](N1[C@@H](C3C=CC=CC=3)COC1=O)=[O:20])=[CH:11]2.CCOC(C)=O.[CH2:39]1[CH2:43]OC[CH2:40]1>[OH-].[Na+]>[CH3:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][C:12]([CH2:17][C@H:18]([CH2:43][CH:39]=[CH2:40])[CH2:19][OH:20])=[CH:11]2

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 8857Ethyl AcetateHCID 21226445Aluminium lithium hydrideHCID 68492500(4S)-3-[3-(5-methylindolyl)propanoyl]-4-phenyl-1,3-oxazolidin-2-one

Product 1

HCID 68489028(2S)-2-[(5-methylindolyl)methyl]pent-4-en-1-olYield 92%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideCatalyst

Conditions

Temperature
-78 °C

Procedure

To a stirred suspension of LiAlH4 (718 mg, 17.90 mmol) in THF (60 mL) was added a precooled solution of 8 (5.78 g, 14.9 mmol) in THF (50 mL) at −78° C. under argon. The mixture was stirred at −78° C. (1 h), then raised to 0° C. (1 h). After an additional 3 h at 0° C., the reaction mixture was cooled to −78° C. and EtOAc (20 mL) was added followed by 10% NaOH (aq) (30 drops). The reaction was quenched by the addition of ice-cold saturated NH4Cl solution (150 mL), extracted with Et2O, washed with brine and dried (Na2SO4). Evaporation provided a residue, which was purified by silica gel flash chromatography to yielded 10 as colorless oil. (3.14 g, 92% yield). H NMR (d6-DMSO) δ 7.32-7.30 (m, 2H), 7.25 (d, 1H, J=2.9 Hz), 6.94 (dd, 1H, J=1.3 Hz & 8.5 Hz), 6.31 (dd, 1H, J=0.8 Hz & 3.1 Hz), 5.78 (m, 1H), 5.04-4.98 (m, 2H), 4.63 (t, 1H, J=5.0), 4.16 (dd, 1H, J=6.9 Hz & 14.2 Hz), 4.02 (dd, 1H, J=6.3 Hz & 14.2 Hz), 3.30-3.23 (m, 2H), 2.36 (s, 3H), 2.09-1.92 (m, 3H). FABMS (+Ve) m/z 229 [M+], 230 [MH+]. Anal. Calcd for C15H19NO C, 78.56; H, 8.35; N, 6.11. Found C, 78.47; H, 8.50; N, 6.16.

Workup

  1. temperatureraised to 0° C. (1 h)
  2. waitAfter an additional 3 h at 0° C.
  3. temperaturethe reaction mixture was cooled to −78° C.
  4. customThe reaction was quenched by the addition of ice-cold saturated NH4Cl solution (150 mL)
  5. extractionextracted with Et2O
  6. washwashed with brine
  7. dry with materialdried (Na2SO4)
  8. customEvaporation
  9. customprovided a residue, which
  10. customwas purified by silica gel flash chromatography

Sources & evidence

ORD record
ord-d06f238ed19b43b4b85dd9c5367771b5
Source dataset
uspto-grants-2010_08
Patent number
US07767645B2

Reaction notes

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