HCID 86235010, compound → HCID 131731106, compound

HRID 1915997Notes

Reaction equation

HRID 1915997 reaction equation
[CH3:1][O:2][CH:3]([O:14][CH3:15])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]=O)=[CH:6][C:5]=1[O:12][CH3:13].[C:16](O[K])([CH3:19])([CH3:18])[CH3:17]>C1COCC1>[CH3:1][O:2][CH:3]([O:14][CH3:15])[C:4]1[CH:9]=[CH:8][C:7](/[CH:10]=[CH:17]/[C:16]2[CH:19]=[CH:9][C:4]([C:3]([O:2][CH3:1])=[O:14])=[CH:5][CH:18]=2)=[CH:6][C:5]=1[O:12][CH3:13]

Participants

4

Reactant 2

HCID 86235010HCID 86235010, compoundHCID 178418922HCID 178418922, compound

Product 1

HCID 131731106HCID 131731106, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The compound was prepared according to the general Horner-Wittig methodology, from 4-formyl-2-methoxybenzaldehyde dimethylacetal (630 mg, 3 mmol), dimethyl-4-carbomethoxylbenzyl phosphonate (775 mg, 1 eq.) using tBuOK (404 mg, 1.2 eq.) as base in anhydrous THF (15 ml); the mixture was heated at 70 C for 90 minutes then worked up as described previously and purified by MPLC with hexanes/ethyl acetate 0-30% gradient. Yield: 795 mg (76%). MS, m/e: 342 (M+) 15%; 311 (M+-MeO, 100%); 294 (5%); 234 (4%); 164 (12%); 139 (10%).

Workup

  1. customThe compound was prepared
  2. temperaturethe mixture was heated at 70 C for 90 minutes
  3. custompurified by MPLC with hexanes/ethyl acetate 0-30% gradient

Sources & evidence

ORD record
ord-a2e3050819c44d12875e5e13b8b70c80
Source dataset
uspto-grants-2013_12
Patent number
US08617515B2

Reaction notes

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