Tetrahydrofuran → HCID 57567185, compound

HRID 1727293Notes

Reaction equation

HRID 1727293 reaction equation
C(N[CH:5]1[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1)(C)C.[CH2:11]([Li])[CH2:12][CH2:13][CH3:14].[Br:16][C:17]1[C:18](=[O:24])[O:19][CH2:20][C:21]=1[O:22][CH3:23].C1C[O:28][CH2:27]C1>>[Br:16][C:17]1[C:18](=[O:24])[O:19][CH:20]([CH:27]([OH:28])[C:7]2[C:6]3[C:5](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:10]=[CH:9][CH:8]=2)[C:21]=1[O:22][CH3:23]

Participants

5

Reactant 4

HCID 8028Tetrahydrofuran3×HCID 62386CyclohexylisopropylamineHCID 817071HCID 817071, compoundHCID 178418339Butyllithium

Product 1

HCID 57567185HCID 57567185, compoundYield 59%

Conditions

Temperature
-78 °C

Procedure

A solution of N-isopropylcyclohexylamine (3.62 g, 4.22 mL, 28.22 mmol) in THF at −78° C. is treated with n-butyl lithium (2.1M in hexane, 13.2 L), and stirred at −78° C. for 0.5 h. The resultant suspension is added dropwise to a suspension of 3-bromo-4-methoxy-5H-furan-2-one (4.95 g, 25.65 mmol) in THF at −78° C. The reaction mixture is stirred at −78° C. for 0.75 h, treated dropwise with a solution of 1-naphthylcarboxaldehyde (4.0 g, 25.65 mmol) in THF, stirred for 0.5 h at −78° C., allowed to warm to 0° C., quenched with saturated NH4Cl and extracted with EtOAc. The extracts are combined, dried over MgSO4 and concentrated in vacuo. The resultant red oil residue is passed through a pad of silica gel using 100% hexanes and 80% EtOAc in hexanes as eluents to afford the title product as a yellow foam, 5.3 g (59% yield), identified by NMR and mass spectral analyses.

Workup

  1. stirringThe reaction mixture is stirred at −78° C. for 0.75 h
  2. stirringstirred for 0.5 h at −78° C.
  3. temperatureto warm to 0° C.
  4. customquenched with saturated NH4Cl
  5. extractionextracted with EtOAc
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-70f31cdf91894b3395da38172547d2a7
Source dataset
uspto-grants-2009_02
Patent number
US07495027B2

Reaction notes

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