Hydrochloric Acid → HCID 11695375, compound

HRID 2375948Notes

Reaction equation

HRID 2375948 reaction equation
[OH:1][C@H:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C@H:11]([OH:14])[CH2:12][CH3:13])[CH2:3][CH3:4].N1C=CC=CC=1.[C:21]1([P:27](Cl)(Cl)=[O:28])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.Cl.[NH+]1C=CC=CC=1.Cl>>[CH2:3]([C@@H:2]1[C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C@H:11]([CH2:12][CH3:13])[O:14][P:27](=[O:28])([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[O:1]1)[CH3:4]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 69990Phenylphosphonic dichlorideHCID 11401308HCID 11401308, compoundHCID 21584435Pyridinium hydrochloride

Product 1

HCID 11695375HCID 11695375, compound

Procedure

To a solution of (R,S)-1-[2-(1-Hydroxy-propyl)-phenyl]-propan-1-ol (1.0 g, 5.15 mmol) in pyridine (1.22 g, 15.4 mmol) was added under exclusion of moisture phenyl phosphonic acid dichloride (1.0 g, 5.15 mmol). There is an exotherm and instant formation of pyridinium hydrochloride. The mixture was stirred over night. By 31P-NMR of the crude mixture there was complete conversion, and only one of two possible diastereoisomers present. After addition of HCl (5 ml of 4 N solution) the product was extracted with TBME (20 ml).

Workup

  1. extractionwas extracted with TBME (20 ml)

Sources & evidence

ORD record
ord-3960aa7d3cdb4f6790ec5d7b91ab8a01
Source dataset
uspto-grants-2008_12
Patent number
US07465838B2

Reaction notes

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