Hydrochloric Acid → HCID 21063916, compound

HRID 2421645Notes

Reaction equation

HRID 2421645 reaction equation
CN1[CH2:6][CH2:5][CH2:4][C:3]1=O.[CH2:8]1[CH2:12][O:11][CH2:10][CH2:9]1.[CH2:13]([Mg]Br)[CH2:14][CH:15]([CH3:17])[CH3:16].Cl.[OH2:21]>>[CH3:10][O:11][C:12](=[O:21])[C:8]1[CH:9]=[CH:6][CH:5]=[C:4]([CH2:13][CH2:14][CH:15]([CH3:17])[CH3:16])[CH:3]=1

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 962WaterHCID 8028TetrahydrofuranHCID 13387N-methyl-2-pyrrolidoneHCID 178418529HCID 178418529, compound

Product 1

HCID 21063916HCID 21063916, compound

Procedure

Compound from example 76A (1.42 g, 5 mmol), N-methylpyrrolidinone (2.8 mL), Fe(acac)3 (120 mg, 0.34 mmol) and dry THF (30 mL) were stirred under nitrogen at room temperature. Isopentylmagnesium bromide (0.46 M in THF, 13 mL) was added by syringe. After stirring for fifteen minutes, HCl 2N (25 mL) was slowly added. The mixture was diluted with water and extracted three times with EtOAc. The organic layers were combined, washed with water and then brine, were dried over MgSO4 and were concentrated. Purification was achieved using flash chromatography on SiO2 with hexanes/EtOAc 98:2. A colourless oil was obtained (848 mg, 82%). NMR 1H (ppm, CDCl3): 7.85-7.81 (m, 2H), 7.37-7.29 (m, 2H), 3.90 (s, 3H), 2.67-2.61 (m, 2H), 1.62-1.46 (m, 3H), 0.92 (d, J3=6.3 Hz, 6H).

Workup

  1. extractionextracted three times with EtOAc
  2. washwashed with water
  3. dry with materialbrine, were dried over MgSO4
  4. concentrationwere concentrated
  5. customPurification
  6. customA colourless oil was obtained (848 mg, 82%)

Sources & evidence

ORD record
ord-b83084dc41bd4c2091308fa34af689d1
Source dataset
uspto-grants-2011_06
Patent number
US07956216B2

Reaction notes

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