Hydrochloric Acid → HCID 27620, compound

HRID 1018980Notes

Reaction equation

HRID 1018980 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH2:13][CH2:14][CH2:15][N:16]3[CH2:25][CH2:24][C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[CH2:17]3)OCC[O:9]2)=[CH:4][CH:3]=1.Cl>CO>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8](=[O:9])[CH2:13][CH2:14][CH2:15][N:16]2[CH2:25][CH2:24][C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH2:17]2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 9905998HCID 9905998, compound

Product 1

HCID 27620HCID 27620, compoundYield 106.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Dioxolane 4A (2.75 g, 6.0 mmol) and 1 M HCl (15 mL) were stirred in MeOH (50 mL) at RT for 3 days. After concentration in vacuo the residue was extracted with EtOAc (400 mL) and 1 M NaOH (100 mL), then H2O (2×50 mL), and brine (25 mL). The solution was dried (Na2SO4), filtered, and concentrated to yield ketone 11A (1.9 g, quant.) as a yellow solid. 13C NMR(300 MHz, CDCl3, δ): 198.60, 165.59 (d, J=254 Hz), 134.85, 134.38, 133.56, 131.65 (d, J=9 Hz), 128.61, 126.56, 126.08, 125.56, 115.52 (d, J=22 Hz), 57.36, 56.08, 50.87, 36.14, 29.12, 21.79.

Workup

  1. concentrationAfter concentration in vacuo the residue
  2. extractionwas extracted with EtOAc (400 mL) and 1 M NaOH (100 mL)
  3. dry with materialThe solution was dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-66f1d7c99ec84b0ea4e86235322649b4
Source dataset
uspto-grants-2002_11
Patent number
US06486173B2

Reaction notes

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