3,4-Dichlorophenol → HCID 22322443, compound

HRID 496868Notes

Reaction equation

HRID 496868 reaction equation
N(C(OCC)=O)=NC(OCC)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl:32][C:33]1[CH:34]=[C:35]([OH:40])[CH:36]=[CH:37][C:38]=1[Cl:39].O[CH:42]1[CH2:47][CH2:46][N:45]([C:48]([O:50][C:51]([CH3:54])([CH3:53])[CH3:52])=[O:49])[CH2:44][CH2:43]1>O1CCCC1>[Cl:32][C:33]1[CH:34]=[C:35]([CH:36]=[CH:37][C:38]=1[Cl:39])[O:40][CH:42]1[CH2:47][CH2:46][N:45]([C:48]([O:50][C:51]([CH3:54])([CH3:53])[CH3:52])=[O:49])[CH2:44][CH2:43]1

Participants

6

Reactant 4

HCID 72583,4-DichlorophenolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylate

Product 1

HCID 22322443HCID 22322443, compoundYield 80.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Diethyl azodicarboxylate (12.6 ml) was added to a solution of triphenylphosphine (20.8 g) in tetrahydrofuran (300 ml) at 0° C. After 15 minutes 3,4-dichlorophenol (12.9 g) was added, after a further 10 minutes tert-butyl 4-hydroxy-1-piperidinecarboxylate (14.5 g) in tetrahydrofuran (100 ml) was added dropwise over 0.5 hour. The solution was stirred at room temperature for 5 hours and concentrated to a small volume. The residue was partitioned between ether and brine. The organic phase was separated, dried and evaporated to a gum. Purification by chromatography (ethyl acetate:isohexane 95:5) gave the sub-titled product as an oil (20 g).

Workup

  1. additionwas added dropwise over 0.5 hour
  2. concentrationconcentrated to a small volume
  3. customThe residue was partitioned between ether and brine
  4. customThe organic phase was separated
  5. customdried
  6. customevaporated to a gum
  7. customPurification by chromatography (ethyl acetate:isohexane 95:5)

Sources & evidence

ORD record
ord-4efa1c111a7d45c88730fc73f32dd2d5
Source dataset
uspto-grants-2005_09
Patent number
US06946478B2

Reaction notes

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