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

HRID 1026140Notes

Reaction equation

HRID 1026140 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-3fb419a1a5ad45fbb5c49740c62fcd64
Source dataset
uspto-grants-2014_05
Patent number
US08729113B2

Reaction notes

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