1-Chloro-3-methoxypropane → Bis(3-methoxypropyl)methylphosphine

HRID 1195625Notes

Reaction equation

[CH3:1][O:2][CH2:3][CH2:4][CH2:5][Mg]Cl.Cl[CH2:9][CH2:10][CH2:11][O:12][CH3:13].Cl[CH:15]([PH2:17])Cl>>[CH3:1][O:2][CH2:3][CH2:4][CH2:5][P:17]([CH2:9][CH2:10][CH2:11][O:12][CH3:13])[CH3:15]

Participants

Reactant 3

HCID 1189271-Chloro-3-methoxypropane

HCID 14511949Dichloromethyl-phosphane

HCID 178495109HCID 178495109, compound

Product 1

HCID 449938Bis(3-methoxypropyl)methylphosphineYield 68%

Procedure

3-Methoxypropyl-magnesium chloride was generated from 1 -chloro-3-methoxypropane (10.0 g, 92.0 mmol) and Mg metal (2.26 g, 93.0 mmol) and reacted with dichloromethylphosphine (4.1 ml, 0.46 mmol) according to General Method I. The residue was purified by fractional distillation (bp=110° C. @2.8 mm Hg) affording 5.9 g (68%) of bis(3-methoxypropyl)methylphosphine as a mobile colorless oil. 31 pNMR(Benzene-d6):δ-43.3. MS (HREI) m/z=192.1279 (192.1279 calc'd for C9H21O2P).

Workup

distillationThe residue was purified by fractional distillation (bp=110° C. @2.8 mm Hg)

Sources & evidence

ORD record: ord-59e07cb8aefc44ac9e84dea751a34122
Source dataset: uspto-grants-1992_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05112594

Reaction notes

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