Tetrahydrofuran → HCID 5368270, compound

HRID 709407Notes

Reaction equation

HRID 709407 reaction equation
C[C:2]([CH3:5])([O-:4])C.[K+].[CH2:7]([O:14][C:15]1[CH:22]=[CH:21][C:18]([CH:19]=O)=[CH:17][CH:16]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C1C[O:26][CH2:25][CH2:24]1>>[CH2:7]([O:14][C:15]1[CH:22]=[CH:21][C:18](/[CH:19]=[CH:24]/[C:25]([O:4][CH2:2][CH3:5])=[O:26])=[CH:17][CH:16]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 78109Benzaldehyde, 4-(phenylmethoxy)-2×HCID 23665647Potassium tert-butoxide

Product 1

HCID 5368270HCID 5368270, compoundYield 95%

Procedure

Triethyl phosphonoacetate (259 mL, 1.3 mol) was added slowly drop wise to a solution of Potassium-tert-butoxide (145 g, 1.29 mol) in dry THF (2 L) at −5° C. and stirred for 30-45 mins. Then a solution of 4-(benzyloxy)benzaldehyde (Intermediate P, 230 g, 1.08 mol) in dry THF (1.5 L) was added slowly drop wise at −10° C. over a period of 15 mins and stirred for 30 mins. After completion, the reaction mixture was poured into ice water (1 L) and extracted with EtOAc (2×1.5 L). The combined organic extracts were washed with sat NaHCO3 solution (1 L), water (1 L), brine (1 L), dried over anhydrous Na2SO4, filtered and evaporated to get crude (E)-ethyl 3-(4-(benzyloxy)phenyl)acrylate (290 g, 95%). The crude was carried to next step without further purification.

Workup

  1. stirringstirred for 30 mins
  2. extractionextracted with EtOAc (2×1.5 L)
  3. washThe combined organic extracts were washed with sat NaHCO3 solution (1 L), water (1 L), brine (1 L)
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-4a9a86f1084c4f858b62ef85863a9d4d
Source dataset
uspto-grants-2015_11
Patent number
US09181198B2

Reaction notes

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