Tetrahydrofuran → HCID 57956847, compound

HRID 1021153Notes

Reaction equation

HRID 1021153 reaction equation
[OH:1][C:2]([CH2:26][CH2:27][CH3:28])([CH2:23][CH2:24][CH3:25])[CH2:3][CH2:4][C:5]1[CH:6]=[C:7]([C:11](=O)[CH2:12][CH2:13][NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH:8]=[CH:9][CH:10]=1.[CH2:29]1COCC1>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[OH:1][C:2]([CH2:26][CH2:27][CH3:28])([CH2:23][CH2:24][CH3:25])[CH2:3][CH2:4][C:5]1[CH:6]=[C:7]([C:11](=[CH2:29])[CH2:12][CH2:13][NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH:8]=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 8028TetrahydrofuranHCID 57956828HCID 57956828, compound

Product 1

HCID 57956847HCID 57956847, compound

Reagents, catalysts & solvents 1

HCID 74505Methyltriphenyliphosphonium bromideCatalyst

Procedure

To a suspension of methyltriphenylphosponium bromide in THF is added KOBu-t (1 M in THF, 6.1 mmol) at room temperature. After stirring for 30 mins, tert-butyl 3-(3-(3-hydroxy-3-propylhexyl)phenyl)-3-oxopropylcarbamate is added. The resulting mixture is stirred at room temperature for 18 h. The reaction is quenched by the addition of AcOH. The mixture is filtered and concentrated under reduced pressure. Purification by flash chromatography (15 to 50% EtOAc-hexanes gradient) gives tert-butyl 3-(3-(3-hydroxy-3-propylhexyl)phenyl)but-3-enylcarbamate.

Workup

  1. stirringThe resulting mixture is stirred at room temperature for 18 h
  2. customThe reaction is quenched by the addition of AcOH
  3. filtrationThe mixture is filtered
  4. concentrationconcentrated under reduced pressure
  5. customPurification by flash chromatography (15 to 50% EtOAc-hexanes gradient)

Sources & evidence

ORD record
ord-792f49599e7941d9922f3157bc6a59bd
Source dataset
uspto-grants-2014_05
Patent number
US08716529B2

Reaction notes

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