Sodium bis(trimethylsilyl)amide → 4-(2,3-Dihydro-1-benzofuran-7-yl)but-3-enoic acid

HRID 594785

Reaction equation

HRID 594785 reaction equation
[Br-].[C:2]([CH2:5][CH2:6][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([OH:4])=[O:3].C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[O:36]1[C:40]2[C:41]([CH:45]=O)=[CH:42][CH:43]=[CH:44][C:39]=2[CH2:38][CH2:37]1>C1COCC1.O>[O:36]1[C:40]2[C:41]([CH:45]=[CH:6][CH2:5][C:2]([OH:4])=[O:3])=[CH:42][CH:43]=[CH:44][C:39]=2[CH2:38][CH2:37]1

Participants

6

Reactant 3

HCID 2724254Sodium bis(trimethylsilyl)amideHCID 2733850(2-Carboxyethyl)triphenylphosphonium bromideHCID 27950182,3-Dihydro-1-benzofuran-7-carbaldehyde

Product 1

HCID 1237713204-(2,3-Dihydro-1-benzofuran-7-yl)but-3-enoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2-carboxyethyl)triphenylphosphonium bromide (617 mg, 1.5 mmol) in THF (20 mL) was added NaHMDS (1.5 mL, 3.0 mmol) at −20° C., and the reaction was stirred for 20 min. 2,3-Dihydro-1-benzofuran-7-carbaldehyde (200 mg, 1.4 mmol) was added to the reaction at −78° C., and the reaction was stirred overnight while warming to rt. The reaction was diluted with water (30 mL) and extracted with EtOAc (3×30 mL). Organics were washed with brine (30 mL), dried (Na2SO4), and concentrated to give the crude title compound as a yellow solid. [M+H] Calc'd for C12H12O3, 205. Found, 205.

Workup

  1. stirringthe reaction was stirred overnight
  2. extractionextracted with EtOAc (3×30 mL)
  3. washOrganics were washed with brine (30 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b52c4e7a83cf4e278251cba40d889ac7
Source dataset
uspto-grants-2016_01
Patent number
US09242968B2

Linked notes

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