Triethylamine → 3-(3-Benzyloxy-phenyl)-2-methoxy-acrylic acid methyl ester

HRID 459311Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:23])[CH:4]([O:21][CH3:22])[CH:5]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:8]=1)O.C(N(CC)CC)C.S(Cl)(C)(=O)=O.C([O-])(=O)C=C.S([O-])(=O)(=O)C>CN(C1C=CN=CC=1)C.ClCCl.C(OCC)C>[CH3:1][O:2][C:3](=[O:23])[C:4]([O:21][CH3:22])=[CH:5][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:8]=1

Participants

Conditions

Temperature: 0 °C

Procedure

The compounds of 3-(3-benzyloxy-phenyl)-3-hydroxy-2-methoxy-propionic acid methyl ester (Example 291, Step 1) (4.06 g, 12.84 mmol), triethylamine (7.15 mL, 51.33 mmol) and 4-(N,N-dimethylamino)pyridine (0.157 g, 128 mmol) were dissolved in dichloromethane (20 mL) in a round bottom flask and then cooled to 0° C. under ice bath. Mesyl chloride (1.093 mL, 14.1 mmol) was added dropwise via syringe, and the mixture was stirred at room temperature until no starting aldol is observed by HPLC-MS (4 days, 0.2 additional mL of MsCl were added each day). The mixture was diluted with 200 mL of diethyl ether, washed with HCl (1N, 3×40 mL) and 40 mL of brine, and dried over MgSO4 Concentration of the mixture afforded 3.96 g. of a 2.5:1 mixture of the acrylate and a single isomer of the mesylate intermediate which was directly used in the next Step. 1H-NMR (CDCl3, 200.15 MHz): 7.46–7.26 (m, 8H), 6.99–6.93 (m, 1H), 5.10 (s, 2H), 3.85 (s, 3H), 3.72 (s, 3H).

Workup

additionwere added each day)
washwashed with HCl (1N, 3×40 mL) and 40 mL of brine
dry with materialdried over MgSO4 Concentration of the mixture
customafforded 3.96 g

Sources & evidence

ORD record: ord-e2159f121cb3420094b10b4f17dd6a6b
Source dataset: uspto-grants-2007_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07192982B2

Reaction notes

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