3-Methylbenzaldehyde → HCID 58598880, compound

HRID 1020320Notes

Reaction equation

HRID 1020320 reaction equation
[CH2:1](OC(=O)C=CC1C=C(C)C=CC=1)C.CO[C:17]1[C:18](Cl)=[CH:19][C:20]2[CH:21]([CH3:29])[CH:22]3[CH2:26][NH:25][CH2:24][CH:23]3[C:27]=2[CH:28]=1.C(OC(=O)CP(OCC(F)(F)F)(OCC(F)(F)F)=O)C.C1OCCOCCOCCOCCOCCOC1.C1(C)C=CC=C(C=O)C=1>C1COCC1>[CH3:1][C:17]1[CH:18]=[CH:19][C:20]2[CH:21]([CH3:29])[CH:22]3[CH2:26][NH:25][CH2:24][CH:23]3[C:27]=2[CH:28]=1

Participants

7

Reactant 5

HCID 121053-MethylbenzaldehydeHCID 2855718-Crown-6HCID 589327Ethyl 3-methylcinnamateHCID 117085025-Methoxy-6-chloro-8-methyl-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrroleHCID 11759356Ethyl [bis(2,2,2-trifluoroethoxy)phosphinyl]acetate

Product 1

HCID 58598880HCID 58598880, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-m-Tolyl-acrylic acid ethyl ester. (Scheme 3) KHMDS (4.0 g, 20.0 mmol) was added to a solution of ethyl[bis(2,2,2-trifluoro-ethoxy)phosphinyl]acetate (4.7 mL, 20.0 mmol) and 18-crown-6 (10.6 g, 40.0 mmol) in THF (200 mL) at −78° C., and stirred for 30 minutes. m-Tolualdehyde (2.1 mL, 18 mmol) was added and the reaction mixture was stirred for 3 hours from −78° C. to room temperature. The reaction was quenched with aqueous hydrochloric acid (1M solution, 100 mL), and the product was extracted with EtOAc (3×100 mL). The organic extracts were washed with brine (100 mL), dried over MgSO4, and concentrated to afford the subtitle compound, which was used without further purification. MS calculated for C12H14O2+H: 191, observed: 191.

Workup

  1. stirringthe reaction mixture was stirred for 3 hours from −78° C. to room temperature
  2. customThe reaction was quenched with aqueous hydrochloric acid (1M solution, 100 mL)
  3. extractionthe product was extracted with EtOAc (3×100 mL)
  4. washThe organic extracts were washed with brine (100 mL)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-df2956738c2140a4a8ce6177e911ca97
Source dataset
uspto-grants-2014_05
Patent number
US08716324B2

Reaction notes

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