Monobenzone → Methyl 3-(4-(2-[4-(benzyloxy)phenoxy]ethyl)phenyl)-2-chloropropanoate

HRID 33814

Reaction equation

C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl:20][CH:21]([CH2:26][C:27]1[CH:32]=[CH:31][C:30]([CH2:33][CH2:34][OH:35])=[CH:29][CH:28]=1)[C:22]([O:24][CH3:25])=[O:23].[CH2:36]([O:43][C:44]1[CH:49]=[CH:48][C:47](O)=[CH:46][CH:45]=1)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1(C)C=CC=CC=1>[CH2:36]([O:43][C:44]1[CH:49]=[CH:48][C:47]([O:35][CH2:34][CH2:33][C:30]2[CH:29]=[CH:28][C:27]([CH2:26][CH:21]([Cl:20])[C:22]([O:24][CH3:25])=[O:23])=[CH:32][CH:31]=2)=[CH:46][CH:45]=1)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

Participants

Conditions

Temperature: 55 °C

Procedure

Triphenylphosphine (2.4 g, 9 mmol) was added to a solution of methyl 2-chloro-3-[4-(2-hydroxyethyl)phenyl]propanoate (2.1 g, 8.5 mmol) and 4-(benzyloxy)phenol (1.7 g, 8 mmol) in 20 ml toluene under nitrogen atmosphere. The solution was warmed to 55° C. and diisopropyl azodicarboxylate (1.8 g, 9 mmol) was added. The reaction mixture was stirred at 55° C. overnight. The mixture was allowed to cool and the solvent was evaporated under reduced pressure. The crude product was purified by flash chromatography using a 80:20 mixture of heptane and EtOAc as eluent to yield 2.28 g of the desired product (yield 61%) as colourless crystals.

Workup

temperatureto cool
customthe solvent was evaporated under reduced pressure
customThe crude product was purified by flash chromatography
additiona 80:20 mixture of heptane and EtOAc as eluent

Sources & evidence

ORD record: ord-b1dbfc4476ed401d93f87254f4a51af6
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07429675B2

Linked notes

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