Pyridine → HCID 86585995, compound

HRID 1794070Notes

Reaction equation

HRID 1794070 reaction equation
[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH2:13][OH:14])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[C:18]([O:20][CH:21]([Cl:23])[CH3:22])=[O:19].N1C=CC=CC=1>C(Cl)Cl>[Cl:23][CH:21]([O:20][C:18](=[O:19])[O:14][CH2:13][C:12]1[CH:11]=[CH:10][C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:16][CH:15]=1)[CH3:22]

Participants

5

Reactant 3

HCID 1049PyridineHCID 70043(4-(Benzyloxy)phenyl)methanolHCID 5213051-Chloroethyl chloroformate

Product 1

HCID 86585995HCID 86585995, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1.07 g (5.0 mmol) 4-benzyloxybenzyl alcohol and 0.786 g (5.5 mmol) 1-chloroethyl chloroformate in 25 ml CH2Cl2 is cooled to 0° C. and 0.435 g (5.5 mmol) pyridine added. After stirring at rt for 2 h the reaction mixture is quenched with 1N HCl, the organic phase separated and washed with sat. NaHCO3 solution and brine, dried over Na2SO4 and evaporated: 1.58 g (98%) (RS)-carbonic acid 4-benzyloxy-benzyl ester 1-chloro-ethyl ester as light yellow oil. 1H-NMR (CDCl3): 1.81 d, J=6 Hz, 3H; 5.07 s, 2H; 5.14 and 5.17, AB-system J=15 Hz, 2H; 6.43 q, J=6 Hz, 1H; 6.97 d, J=8.5 Hz, 2H and 7.30–7.45 m, 7H.

Workup

  1. customis quenched with 1N HCl
  2. customthe organic phase separated
  3. washwashed with sat. NaHCO3 solution and brine
  4. dry with materialdried over Na2SO4
  5. customevaporated
  6. custom6.97 d, J=8.5 Hz, 2H and 7.30–7.45 m, 7H

Sources & evidence

ORD record
ord-4d8329702b364751964253a04feef464
Source dataset
uspto-grants-2006_04
Patent number
US07022707B2

Reaction notes

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