Triethylamine → (2-Methyl-pent-4-en-2-oxy)diphenylphosphine

HRID 1807925Notes

Reaction equation

HRID 1807925 reaction equation
[CH3:1][C:2]([OH:7])([CH2:4][CH:5]=[CH2:6])[CH3:3].C(N(CC)CC)C.Cl[P:16]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C1COCC1.CN(C)C1C=CN=CC=1>[CH3:1][C:2]([O:7][P:16]([C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)([CH2:4][CH:5]=[CH2:6])[CH3:3]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 66180ChlorodiphenylphosphineHCID 1364402-Methyl-4-penten-2-ol

Product 1

HCID 59173107(2-Methyl-pent-4-en-2-oxy)diphenylphosphineYield 56%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 2-methyl-pent-4-en-2-ol (5.0 g; CAS 624-97-5) in THF (50 ml) were added sequentially 4-dimethylaminopyridine (1.22 g), triethylamine (8.32 ml) and chlorodiphenylphosphine (10.2 ml). The resulting mixture was stirred at room temperature overnight. The reaction mixture was evaporated and purified by column chromatography (basic alumina; gradient: heptane/EtOAc) to give (2-methyl-pent-4-en-2-oxy)diphenylphosphine (8.0 g, 56%) as a colourless oil which was used immediately in the next step.

Workup

  1. customThe reaction mixture was evaporated
  2. custompurified by column chromatography (basic alumina; gradient: heptane/EtOAc)

Sources & evidence

ORD record
ord-d6c9dbd4d0db41fba34a69dd70e3fc1e
Source dataset
uspto-grants-2013_01
Patent number
US08357712B2

Reaction notes

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