Triethylamine → Naphthalen-1-yl-carbamic acid 4-hydroxy-4-phenyl-butyl ester

HRID 1601331Notes

Reaction equation

HRID 1601331 reaction equation
[C:1]1([N:11]=[C:12]=[O:13])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[C:14]1([CH:20]([OH:25])[CH2:21][CH2:22][CH2:23][OH:24])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(N(CC)CC)C>C(Cl)Cl>[OH:25][CH:20]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:21][CH2:22][CH2:23][O:24][C:12](=[O:13])[NH:11][C:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 66589alpha-Naphthyl isocyanateHCID 2638511-Phenyl-1,4-butanediol

Product 1

HCID 54207492Naphthalen-1-yl-carbamic acid 4-hydroxy-4-phenyl-butyl esterYield 77%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1-Naphthyl isocyanate (4.3 ml, 30 mmol) in 50 ml of methylene chloride was added under nitrogen dropwise over 1 hour to a solution of 4-phenyl-4-hydroxybutanol (5.00 g, 30 mmol), prepared in step (a) of Example 6, and triethylamine (4.2 ml, 30 mmol) in 200 ml of methylene chloride at room temperature. After the addition the reaction was stirred at room temperature for 18 hours. The solid present in the reaction was removed by filtration. The filtrate was extracted with 1 N HCl, dried (MgSO4) and the solvent removed under reduced pressure to give 10.08 g of a clear oil Purification of the oil by chromatography on 1 kg of silica gel (230-400 mesh) using 3%-20% ethyl acetate-methylene chloride as the eluent gave naphthalen-1-yl-carbamic acid 4-hydroxy-4-phenyl-butyl ester (7.73 g, 77%) as a white solid, mp 92-92° C.

Workup

  1. additionAfter the addition the reaction
  2. customThe solid present in the reaction was removed by filtration
  3. extractionThe filtrate was extracted with 1 N HCl
  4. dry with materialdried (MgSO4)
  5. customthe solvent removed under reduced pressure
  6. customto give
  7. custom10.08 g of a clear oil Purification of the oil by chromatography on 1 kg of silica gel (230-400 mesh)

Sources & evidence

ORD record
ord-d5665cde08144db38d86a17298bbd9a1
Source dataset
uspto-grants-1999_11
Patent number
US05977170

Reaction notes

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