Benzyl Alcohol → HCID 18403062, compound

HRID 377179Notes

Reaction equation

HRID 377179 reaction equation
[CH2:1]([O:8][C:9]([CH:11]([CH2:16][CH2:17][C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19])[CH2:12][PH:13](=[O:15])[OH:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:28](O)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.CN(C1C=CC=CN=1)C.C1(N=C=NC2CCCCC2)CCCCC1>O1CCCC1>[CH2:1]([O:8][C:9]([CH:11]([CH2:16][CH2:17][C:18]([O:20][CH2:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)=[O:19])[CH2:12][P:13]([CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)(=[O:14])[OH:15])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 244Benzyl Alcohol2×HCID 10868DicyclohexylcarbodiimideHCID 218852-DimethylaminopyridineHCID 178520628HCID 178520628, compound

Product 1

HCID 18403062HCID 18403062, compoundYield 48.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 2,4-di-(benzyloxycarbonyl)butyl phosphinic acid (6) (19.3 g, 49.4 mmol) in tetrahydrofuran was added benzyl alcohol (5.3 g, 49.3 mmol) and dimethylamino in tetrahydrofuran was added benzyl alcohol (5.3 g, 49.3 mmol) and dimethylamino pyridine (0.5 g). Dicylcohexylcarbodimide (DCC, 12 g, 58 mmol) was added and a white precipitate formed. After 30 minutes the white suspension was filtered and the filtrate evaporated under reduced pressure. The clear and colorless oil was purified by flash chromatography and eluted with 1:1 Hex./EtOAc to give 2,4-di(benzyloxycarbonyl)butylbenzylphosphinic acid (7) (11.5 g, 47w) as a clear and colorless oil. Rf. 0.16 (1:1 Hex./EtOAc);

Workup

  1. customa white precipitate formed
  2. filtrationAfter 30 minutes the white suspension was filtered
  3. customthe filtrate evaporated under reduced pressure
  4. customThe clear and colorless oil was purified by flash chromatography
  5. washeluted with 1:1 Hex

Sources & evidence

ORD record
ord-b351c5dad233443086ea968680524eed
Source dataset
uspto-grants-2000_02
Patent number
US06025344

Reaction notes

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