Benzyl Alcohol → HCID 15042555, compound

HRID 1722675Notes

Reaction equation

HRID 1722675 reaction equation
[C:1]([C:5]([CH3:11])([CH3:10])[CH2:6]C(O)=O)([O:3][CH3:4])=[O:2].C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:19])C=CC=CC=1.C([N:31]([CH2:34]C)CC)C.[CH2:36]([OH:43])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>C1(C)C=CC=CC=1>[CH2:36]([O:43][C:34]([NH:31][CH2:6][C:5]([CH3:11])([CH3:10])[C:1]([O:3][CH3:4])=[O:2])=[O:19])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 150395654-Methoxy-3,3-dimethyl-4-oxobutanoic acid

Product 1

HCID 15042555HCID 15042555, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

3-Carbomethoxy-3-methylbutanoic acid [Bull. Soc. Chim. Fr., 828 (1965), 7.85 g, 0.049 mol]was reacted with diphenylphosphorylazide and triethylamine as described in Example 102. After heating the toluene solution for 1.5 h, benzyl alcohol (8 g) was added directly to the reaction mixture and heating at reflux was continued for 20 h. Work-up and chromatography gave methyl 3-benzyloxycarbonylamino-2,2-dimethylpropionate. NMR (300 MHz, CDCl3): 1.2 (s,6H), 3.3 (d,2H), 3.68 (s,3H), 5.1 (s,2H), 5.22 (m,1H). A sample of the methyl ester (6.21 g, 0.023 mol) was saponified with 3.1 g (0.78 mol) of NaOH in 100 ml ethanol/10 ml H2O at room temperature for 48 h. Work-up as in Example 102 gave the desired product as a liquid. NMR (300 MHz, CDCl3): 1.23 (s,6H), 3.32 (d,2H), 5.10 (s,2H), 5.27 (m,1H).

Workup

  1. temperatureheating
  2. temperatureat reflux

Sources & evidence

ORD record
ord-90534470336b466d9f6a717d90381cdf
Source dataset
uspto-grants-1989_08
Patent number
US04857507

Reaction notes

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