Trichloroethanol → 3-[4-(tert-Butyl-dimethyl-silanyloxymethyl)-phenyl]-2-ethoxy-propionic acid 2,2,2-trichloro-ethyl ester

HRID 1628158Notes

Reaction equation

HRID 1628158 reaction equation
[C:1]([SiH2:5][O:6][C:7]([CH3:23])([CH3:22])[C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH:15]([O:19][CH2:20][CH3:21])[C:16]([OH:18])=[O:17])=[CH:10][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].[Cl:24][C:25]([Cl:29])([Cl:28])[CH2:26]O>C(Cl)Cl.CN(C1C=CN=CC=1)C>[Cl:24][C:25]([Cl:29])([Cl:28])[CH2:26][O:17][C:16](=[O:18])[CH:15]([O:19][CH2:20][CH3:21])[CH2:14][C:11]1[CH:12]=[CH:13][C:8]([C:7]([CH3:22])([CH3:23])[O:6][SiH2:5][C:1]([CH3:3])([CH3:4])[CH3:2])=[CH:9][CH:10]=1

Participants

5

Reactant 2

HCID 8259TrichloroethanolHCID 1317316813-[4-(tert-Butyl-dimethyl-silanyloxymethyl)-phenyl]-2-ethoxy-propionic acid

Product 1

HCID 1317316833-[4-(tert-Butyl-dimethyl-silanyloxymethyl)-phenyl]-2-ethoxy-propionic acid 2,2,2-trichloro-ethyl ester

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

Under nitrogene atmosphere 3-[4-(tert-butyl-dimethyl-silanyloxymethyl)-phenyl]-2-ethoxy-propionic acid (0.135 g, 0.4 mmol) and 2,2,2-trichloro ethanol (0.06 g, 0 4 mmol) were dissolved in dry DCM (5 mL) and DMAP (2 mg, 0.02 mmol) was added followed by EDCxHCl (0.092 g, 0.48 mmol) at 0° C. The mixture was stirred for 18 h at ambient temperature, then diluted with DCM and extracted with aq. HCl (2N) and water. The organic layer was separated, dried (MgSO4) and evaporated to afford the crude product which was used in the next step without further purification (0.176 g, 93.6%). 1H NMR (400 MHz, CDCl3): δ 7.12-7.19 (m, 4H), 4.62-4.71 (q, 2H), 4.63 (s, 2H), 4.05-4.08 (m, 1H), 3.55-3.59 (m, 1H), 3.27-3.31 (m, 1H), 2.92-3.03 (m, 2H), 1.08 (t, 3H).

Workup

  1. customfollowed by EDCxHCl (0.092 g, 0.48 mmol) at 0° C
  2. extractionextracted with aq. HCl (2N) and water
  3. customThe organic layer was separated
  4. dry with materialdried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-c40c14febf254fc0a44022babd6eefa3
Source dataset
uspto-grants-2014_07
Patent number
US08785681B2

Reaction notes

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