Hydrochloric Acid → HCID 90003554, compound

HRID 587858Notes

Reaction equation

HRID 587858 reaction equation
C[O:2][CH:3]=[CH:4][C@@H:5]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]2(OCC[O:15]2)[CH2:6]1.Cl>O1CCCC1>[O:15]=[C:7]1[C:8]2[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:14][C@@H:5]([CH2:4][CH:3]=[O:2])[CH2:6]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 131734415HCID 131734415, compound

Product 1

HCID 90003554HCID 90003554, compoundYield 67.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of (R)-3′-(2-methoxyvinyl)-3′,4′-dihydro-2′H-spiro[[1,3]dioxolane-2,1′-naphthalene] (step-4) (3.5 g, 14.21 mmol) in tetrahydrofuran (20 mL) was added HCl (2.159 mL, 71.1 mmol) at 25° C. and reaction was stirred for 16 h. Reaction was monitored by TLC. After completion solvent was evaporated at reduced pressure. Crude obtained was purified by column chromatography (Biotage) using eluent 30% ethyl acetate/hexane to give (S)-2-(4-oxo-1,2,3,4-tetrahydronaphthalen-2-yl)acetaldehyde (1.8 g, 9.56 mmol, 67.3% yield) as colourless sticky compound; GCMS 188.10.

Workup

  1. customreaction
  2. customReaction
  3. customAfter completion solvent was evaporated at reduced pressure
  4. customCrude obtained
  5. customwas purified by column chromatography (Biotage)

Sources & evidence

ORD record
ord-0794fa53cb1b495a99cc5f4396067275
Source dataset
uspto-grants-2016_01
Patent number
US09227919B2

Reaction notes

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