Potassium Carbonate → (5'-Carbomethoxy-[1,1';3',1'']terphenyl-2'-yloxy)-acetic acid tert-butyl ester

HRID 1743418Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:23])[C:4]1[CH:9]=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:7]([OH:16])=[C:6]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:5]=1.Br[CH2:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27].C([O-])([O-])=O.[K+].[K+]>C(#N)C>[C:29]([O:28][C:26](=[O:27])[CH2:25][O:16][C:7]1[C:6]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:5][C:4]([C:3]([O:2][CH3:1])=[O:23])=[CH:9][C:8]=1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)([CH3:32])([CH3:31])[CH3:30]

Participants

Conditions

Temperature: 70 °C

Procedure

To the phenol from Step 2 (3.50 g, 11.5 mmol) in acetonitrile (40 mL) was added tert-butyl bromoacetate (3.39 mL, 23 mmol) and K2CO3 (1.93 g, 12.65 mmol). The mixture was heated for 2 h at 70° C. then cooled to room temperature and concentrated. The residue was partitioned between ethyl acetate/H2O. The organic phase was dried (MgSO4) and concentrated to give crude product. The compound was purified by passing it through a short filter column (SiO2) using hexane as the elutant. Concentration afforded 4.63 g (96%) of product as a clear oil. 1H NMR (DMSO-d6) δ 7.86 (s, 2H), 7.60–7.40 (m, 10H), 3.85 (2s, 5H), 1.19 (s, 9H).

Workup

temperaturethen cooled to room temperature
concentrationconcentrated
customThe residue was partitioned between ethyl acetate/H2O
dry with materialThe organic phase was dried (MgSO4)
concentrationconcentrated
customto give crude product
customThe compound was purified
filtrationa short filter column (SiO2)
concentrationConcentration

Sources & evidence

ORD record: ord-4be8838e19c649b5b54a90cf959de1e9
Source dataset: uspto-grants-2006_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07008636B2

Reaction notes

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