Benzyl Alcohol → HCID 86745101, compound

HRID 728901Notes

Reaction equation

HRID 728901 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[CH:16]([NH:18]/[C:19](=[CH:23]/[CH:24]([CH3:36])[CH2:25][P:26]([O:32][CH:33]([CH3:35])[CH3:34])([O:28][CH:29]([CH3:31])[CH3:30])=[O:27])/[C:20]([OH:22])=[O:21])=[O:17].[CH2:37](O)[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1>CN(C1C=CN=CC=1)C.ClCCl>[CH:16]([NH:18][CH:19](/[CH:23]=[C:24](\[CH3:36])/[CH2:25][P:26]([O:28][CH:29]([CH3:30])[CH3:31])([O:32][CH:33]([CH3:35])[CH3:34])=[O:27])[C:20]([O:22][CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)=[O:21])=[O:17]

Participants

6

Reactant 3

HCID 244Benzyl AlcoholHCID 10868DicyclohexylcarbodiimideHCID 86745102HCID 86745102, compound

Product 1

HCID 86745101HCID 86745101, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

11.5 g (56.4 mmols) of dicyclohexylcarbodiimid are added to a solution of 18.1 g (56.4 mmols) of E-2-formylamino-4-methyl-5-diisopropylphosphono-pentenoic acid, 6.1 g (56.4 mmols) of benzyl alcohol and 0.7 g of 4-(N,N-dimethylamino)pyridine in 140 ml of dichloromethane. The reaction mixture is stirred 2 hours in an ice bath and 10 hours at room temperature. The reaction solution is filtrated clear, washed with diluted hydrochloric acid and twice with water, dried over magnesium sulfate and chromatographed over silica gel with first ethyl acetate and then ethyl acetate/isopropanol as eluent. Benzyl E-2-formylamino-4-methyl-5-diisopropylphosphono-3-pentenoate is obtained as an orange-colored oil which can be crystallized from diethyl ether/hexane; m.p. 50°-58°.

Workup

  1. filtrationThe reaction solution is filtrated clear
  2. washwashed with diluted hydrochloric acid and twice with water
  3. dry with materialdried over magnesium sulfate
  4. customchromatographed over silica gel with first ethyl acetate

Sources & evidence

ORD record
ord-2cae6a9d6bee462088bbd704db5af2d2
Source dataset
uspto-grants-1991_09
Patent number
US05051413

Reaction notes

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