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

HRID 1195636Notes

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° [email protected] mm Hg) affording 5.9 g (68%) of bis(3-methoxypropyl)methylphosphine as a mobile colorless oil. 31PNMR(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° [email protected] mm Hg)

Sources & evidence

ORD record: ord-26fa5e99ac904fbfb3f9f86fdd20e847
Source dataset: uspto-grants-1992_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05112595

Reaction notes

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