Triethyl phosphite → HCID 15341133, compound

HRID 1720854Notes

Reaction equation

[CH3:1][C:2]1[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][C:3]=1[CH:4](Br)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[P:17]([O:24]CC)([O:21][CH2:22][CH3:23])[O:18][CH2:19][CH3:20]>>[CH3:1][C:2]1[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][C:3]=1[CH:4]([P:17](=[O:24])([O:21][CH2:22][CH3:23])[O:18][CH2:19][CH3:20])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

Reactant 2

HCID 31215Triethyl phosphite

HCID 22416497HCID 22416497, compound

Product 1

HCID 15341133HCID 15341133, compoundYield 98.9%

Procedure

A solution of 2,5-dimethylbenzhydryl bromide (64.2 g, 233 mmol) prepared according to Example 3, was heated at 155° C., under N2, in triethyl phosphite (60.0 mL, 350 mmol), for 16 hours. The excess triethyl phosphite was removed by distillation to give 76.6 g of a pale yellow oil. The crude product was chromatographed on a silica gel column. Elution with ethyl acetate/hexane (1:1) afforded analytically pure product as a pale yellow oil, 57.36 g (74.0%). 300 MHz 1H NMR (CDCl3): δ, 4.64 (d,1H, J=26.0 Hz, PCH), 2.33 (s, 3H, PhCH3), 2.28 (s, 3H, PhCH3). MS: 333 (M+1).

Workup

customThe excess triethyl phosphite was removed by distillation

Sources & evidence

ORD record: ord-bdb4cb567e7846d289399f7d80f835ed
Source dataset: uspto-grants-1996_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05508273

Reaction notes

Loading…