Benzyl Alcohol → HCID 86585468, compound

HRID 2304990Notes

Reaction equation

HRID 2304990 reaction equation
C([C:4]([CH3:31])([CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])=[CH:19][CH:18]=1)[CH2:5][CH2:6][P:7](=[O:14])([O:11][CH2:12][CH3:13])[O:8][CH2:9][CH3:10])(O)=O.C([N:34]([CH2:37]C)CC)C.ClC(OC)=[O:41].[N-]=[N+]=[N-].[Na+].[CH2:48]([OH:55])[C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1>O1CCCC1.O.C1(C)C=CC=CC=1>[CH2:9]([O:8][P:7]([CH2:6][CH2:5][C:4]([NH:34][C:37]([O:55][CH2:48][C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1)=[O:41])([CH3:31])[CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])=[CH:19][CH:18]=1)(=[O:14])[O:11][CH2:12][CH3:13])[CH3:10]

Participants

9

Reactant 5

HCID 244Benzyl AlcoholHCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 33557Sodium AzideHCID 18459226HCID 18459226, compound

Product 1

HCID 86585468HCID 86585468, compoundYield 47.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of (±)-diethyl 3-carboxy-3-methyl-5-(4-(octyl)phenyl)pentylphosphonate (0.165 g, 0.362 mmol) in tetrahydrofuran (1 ml) at 0° C. was added triethylamine (0.061 ml, 0.434 mmol) followed by methyl chloroformate (0.053 ml, 0.699 mmol). After stirring for 15 min, sodium azide (0.071 g, 1.08 mmol) in water (1 ml) was added. The ice bath was removed and the reaction stirred for 1 h. The reaction was diluted with ethyl acetate (25 ml) and washed with 2N aq HCl (25 ml), saturated aqueous sodium chloride (25 ml), dried over magnesium sulfate and concentrated to give a colorless oil. This oil was dissolved in toluene (1 ml), benzyl alcohol (0.056 ml, 0.543 mmol) was added and the solution heated to 90° C. for 4 h. The reaction was cooled, placed onto silica gel and eluted with hexane/acetone (70:30) to give a colorless oil (0.097 g): MS m/e 560.4 (M+).

Workup

  1. customThe ice bath was removed
  2. stirringthe reaction stirred for 1 h
  3. additionThe reaction was diluted with ethyl acetate (25 ml)
  4. washwashed with 2N aq HCl (25 ml), saturated aqueous sodium chloride (25 ml)
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customto give a colorless oil
  8. temperatureThe reaction was cooled
  9. washeluted with hexane/acetone (70:30)

Sources & evidence

ORD record
ord-a5310db4b22346499a4b030d86b104e5
Source dataset
uspto-grants-2002_08
Patent number
US06437165B1

Reaction notes

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