1,8-Diazabicyclo(5.4.0)undec-7-ene → (Z)-ethyl 3-(4-(benzyloxy)-3,5-difluorophenyl)-2-ethoxyacrylate

HRID 445853Notes

Reaction equation

HRID 445853 reaction equation
[Cl-].[CH2:2]([O:4][CH:5]([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:3].C1CCN2C(=NCCC2)CC1.[CH2:41]([O:48][C:49]1[C:56]([F:57])=[CH:55][C:52]([CH:53]=O)=[CH:51][C:50]=1[F:58])[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1>O1CCCC1>[CH2:41]([O:48][C:49]1[C:56]([F:57])=[CH:55][C:52](/[CH:53]=[C:5](\[O:4][CH2:2][CH3:3])/[C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:51][C:50]=1[F:58])[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 11327835Phosphonium, (1,2-diethoxy-2-oxoethyl)triphenyl-, chloride (1:1)HCID 157140264-(Benzyloxy)-3,5-difluorobenzaldehyde

Product 1

HCID 59419855(Z)-ethyl 3-(4-(benzyloxy)-3,5-difluorophenyl)-2-ethoxyacrylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (1,2-diethoxy-2-oxoethyl)triphenylphosphonium chloride (679) (1.61 g, 3.76 mmol) in tetrahydrofuran (56 mL) was added DBU (0.67 ml, 4.51 mmol) and the reaction was stirred for 10 minutes at room temperature. 4-(benzyloxy)-3,5-difluorobenzaldehyde (1.40 g, 5.64 mmol) was added in one portion and the reaction was stirred at room temperature for 18 hours. The solvent was removed in vacuo, diethyl ether was added and the solids filtered. The filtrate was concentrated in vacuo and the residue oil was purified by flash column chromatography (0-30% EtOAc in hexanes) to provide (Z)-ethyl 3-(4-(benzyloxy)-3,5-difluorophenyl)-2-ethoxyacrylate (680).

Workup

  1. stirringthe reaction was stirred at room temperature for 18 hours
  2. customThe solvent was removed in vacuo, diethyl ether
  3. additionwas added
  4. filtrationthe solids filtered
  5. concentrationThe filtrate was concentrated in vacuo
  6. customthe residue oil was purified by flash column chromatography (0-30% EtOAc in hexanes)

Sources & evidence

ORD record
ord-1d36fda940f947a6938d4610e361ffa0
Source dataset
uspto-grants-2013_07
Patent number
US08476308B2

Reaction notes

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