Formaldehyde → HCID 11596500, compound

HRID 1360019Notes

Reaction equation

HRID 1360019 reaction equation
[CH3:1][O:2][C:3](=[O:28])/[C:4](/[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH2:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([NH:22][CH2:23][CH:24]([CH3:26])[CH3:25])=[CH:18][C:17]=1[F:27])=[CH:5]/[O:6][CH3:7].[BH-](OC(C)=O)(OC(C)=O)O[C:31](C)=O.[Na+].C=O.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:28])/[C:4](/[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH2:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([N:22]([CH2:23][CH:24]([CH3:26])[CH3:25])[CH3:31])=[CH:18][C:17]=1[F:27])=[CH:5]/[O:6][CH3:7]

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 11617976HCID 11617976, compound

Product 1

HCID 11596500HCID 11596500, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

70 mg (0.18 mmol) of the compound obtained in Step 3 was dissolved in 1.5 ml of methylene chloride, and 57 mg (0.27 mmol) of NaBH(OAc)3 and 30 μl (0.40 mmol) of formaldehyde were added thereto. After stirring at room temperature for 22 hours, the reaction mixture was treated with a saturated sodium bicarbonate aqueous solution, and the water layer was separated and extracted twice with 10 ml of methylene chloride. The organic layers were combined, dried over anhydrous MgSO4, and concentrated under a reduced pressure. The residue was subjected to column chromatography using 20% ethyl acetate/hexane as an eluent to obtain 50 mg (yield 73%) of (E)-methyl-2-[2-((4-(N-isobutyl-N-methylamino)-2-fluorophenoxy)methyl)phenyl]-3-methoxyacrylate as an oil.

Workup

  1. customthe water layer was separated
  2. extractionextracted twice with 10 ml of methylene chloride
  3. dry with materialdried over anhydrous MgSO4
  4. concentrationconcentrated under a reduced pressure

Sources & evidence

ORD record
ord-0b08bc7eed9d4b8f89f1506c12b150a4
Source dataset
uspto-grants-2011_02
Patent number
US07879835B2

Reaction notes

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