Hydrochloric Acid → HCID 18443703, compound

HRID 459264Notes

Reaction equation

HRID 459264 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[CH2:11]([O:18][C:19]1[CH:26]=[CH:25][C:22]([CH:23]=[O:24])=[CH:21][CH:20]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[CH3:27][O:28][CH2:29][C:30]([O:32][CH3:33])=[O:31].Cl>C1COCC1.O>[OH:24][CH:23]([C:22]1[CH:21]=[CH:20][C:19]([O:18][CH2:11][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[CH:26][CH:25]=1)[CH:29]([O:28][CH3:27])[C:30]([O:32][CH3:33])=[O:31]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 78109Benzaldehyde, 4-(phenylmethoxy)-HCID 80507Methyl methoxyacetateHCID 2724254Sodium bis(trimethylsilyl)amide

Product 1

HCID 18443703HCID 18443703, compoundYield 105.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Sodium bis-(trimethylsilyl)amide (440 mL 0.44 mol 1.0 M in THF) was cooled to −70° C. under a nitrogen atmosphere. A solution of 4-benzyloxybenzaldehyde (85 g, 0.4 mol) and methyl methoxyacetate (52 g, 0.5 mol) in THF (0.5 L) was added dropwise at −70° C. over 2 hours, and the mixture was stirred for an hour. A solution of concentrated HCl (85 mL) and water (85 mL) was added at −70° C. The resulting solution was allowed to warm to ambient temperature and was extracted with MTBE (2×0.5 L). The combined extracts were washed with brine (0.5 L), dried (MgSO4), filtered, and concentrated under to give 133 g of a red oil.

Workup

  1. extractionwas extracted with MTBE (2×0.5 L)
  2. washThe combined extracts were washed with brine (0.5 L)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated under

Sources & evidence

ORD record
ord-662a304bcf504a03bcc48a05f80ca427
Source dataset
uspto-grants-2007_03
Patent number
US07192982B2

Reaction notes

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