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

HRID 885190Notes

Reaction equation

HRID 885190 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-54f5a451de13426983b50ef866ae508a
Source dataset
uspto-grants-2012_08
Patent number
US08242153B2

Reaction notes

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