Hydrochloric Acid → 5-(3-(1-hydroxyethyl)-1-oxo-1H-isochromen-4-yl)thiophene-2-carbaldehyde

HRID 634368Notes

Reaction equation

HRID 634368 reaction equation
[OH:1][CH:2]([C:4]1[O:5][C:6](=[O:28])[C:7]2[C:12]([C:13]=1[C:14]1[S:15][C:16]([CH:19]3OC(C)(C)C(C)(C)[O:20]3)=[CH:17][CH:18]=1)=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH3:3].Cl>CC#N.O.CCOC(C)=O>[OH:1][CH:2]([C:4]1[O:5][C:6](=[O:28])[C:7]2[C:12]([C:13]=1[C:14]1[S:15][C:16]([CH:19]=[O:20])=[CH:17][CH:18]=1)=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH3:3]

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 1181312903-(1-hydroxyethyl)-4-(5-(4,4,5,5-tetramethyl-1,3-dioxolan-2-yl)thiophen-2-yl)-1H-isochromen-1-one

Product 1

HCID 1181311385-(3-(1-hydroxyethyl)-1-oxo-1H-isochromen-4-yl)thiophene-2-carbaldehydeYield 99.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-(1-hydroxyethyl)-4-(5-(4,4,5,5-tetramethyl-1,3-dioxolan-2-yl)thiophen-2-yl)-1H-isochromen-1-one (Intermediate B29, 940 mg, 2.347 mmol) was dissolved in 20 ml of MeCN and 20 ml of HCl 1M were added. The clear yellow solution was stirred overnight at rt. The mixture was diluted with 50 ml of water and 200 ml of EtOAc were added. then stirred for 20 min. Phases were separated and the organic one was washed again with 100 ml of NaHCO3 sat. sol. Phases were separated again and the organic one was dried over sodium sulfate, filtered and concentrated to dryness to leave 5-(3-(1-hydroxyethyl)-1-oxo-1H-isochromen-4-yl)thiophene-2-carbaldehyde (700 mg, 2.331 mmol, 99% yield) as a yellow fluffy solid

Workup

  1. additionwere added
  2. stirringthen stirred for 20 min
  3. customPhases were separated
  4. washthe organic one was washed again with 100 ml of NaHCO3 sat. sol. Phases
  5. customwere separated again
  6. dry with materialthe organic one was dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-1e4630e7a0144e158be92ab7db5d8f70
Source dataset
uspto-grants-2016_04
Patent number
US09321776B2

Reaction notes

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