Benzyl Alcohol → HCID 67918807, compound

HRID 728900Notes

Reaction equation

HRID 728900 reaction equation
C[Si](Br)(C)C.C([NH:8][CH:9](/[CH:20]=[C:21](\[CH3:33])/[CH2:22][P:23]([O:29]C(C)C)([O:25]C(C)C)=[O:24])[C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11])=O.C(O)C1C=CC=CC=1>ClCCl>[NH2:8]/[C:9](=[CH:20]/[CH:21]([CH3:33])[CH2:22][P:23]([OH:29])([OH:25])=[O:24])/[C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11]

Participants

5

Reactant 3

HCID 244Benzyl AlcoholHCID 76113BromotrimethylsilaneHCID 86745101HCID 86745101, compound

Product 1

HCID 67918807HCID 67918807, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

23 ml (178 mmols) of trimethylsilyl bromide are added dropwise at room temperature to a solution of 18.3 g (44.5 mmols) of benzyl E-2-formylamino-4-methyl-5-diisopropylphosphono-3-pentenoate in 73 ml of dichloromethane. After 20 hours at room temperature 46 ml of benzyl alcohol are added dropwise, and the reaction mixture is allowed to stand for additional 20 hours at room temperature. The dichloromethane is distilled off, first 40 ml of ethanol and then dropwise 40 ml of propyleneoxide in 40 ml of ethanol are added. The crystalline precipitate formed is filtered off, triturated with 200 ml of water and filtrated off again. Benzyl E-2-amino-4-methyl-5-phosphono-pentenoate of m.p. 196°-197° (decomp.) is thus obtained.

Workup

  1. distillationThe dichloromethane is distilled off
  2. additionfirst 40 ml of ethanol and then dropwise 40 ml of propyleneoxide in 40 ml of ethanol are added
  3. customThe crystalline precipitate formed
  4. filtrationis filtered off
  5. customtriturated with 200 ml of water
  6. filtrationfiltrated off again

Sources & evidence

ORD record
ord-a8bb93090a6040fa9740ebf83bfee777
Source dataset
uspto-grants-1991_09
Patent number
US05051413

Reaction notes

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