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Isobutylene → HCID 22241519, compound

HRID 892220
Notes
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Reaction equation

HRID 892220 reaction equation
[CH3:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][O:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH2:19][C:20]3[N:29]([CH3:30])[C:28](=[O:31])[C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[N:21]=3)[CH:13]=2)[C:3]=1[CH:4]=[O:5].C=C(C)C.[O-:36]Cl=O.[Na+]>C(O)(C)(C)C.O.C(OCC)(=O)C>[CH3:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][O:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH2:19][C:20]3[N:29]([CH3:30])[C:28](=[O:31])[C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[N:21]=3)[CH:13]=2)[C:3]=1[C:4]([OH:36])=[O:5]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 8255IsobutyleneHCID 22241385HCID 22241385, compoundHCID 23668197Sodium Chlorite

Product 1

HCID 22241519HCID 22241519, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6386tert-Butanol
Solvent
HCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 2-methyl-6-[3-(3-methyl-4-oxo-3,4-dihydro-quinazolin-2-ylmethoxy)phenoxymethyl]-benzaldehyde (120 mg, 0.28 mmol, example 102) in t-butanol (1.5 mL) is added iso-butene (0.5 mL) followed by NaClO2 (220 mg, tech grade 1.6 mmol) in water (1.5 mL) and NaH2PO4.H2O (220 mg, 1.6 mmol) in water (1.5 mL). This mixture is stirred for 1 h (during which time the solids dissolve) then diluted with ethyl acetate, washed with water and brine, dried over MgSO4 and concentrated. The residue is purified by flash chromatography (10% methanol in dichloromethane). This product was suspended in chloroform and filtered through celite. The filtrate is concentrated under reduced pressure to give the title compound as an amorphous solid. 1H NMR (300 MHz, CDCl3): δ 8.41 (d, 1H), 7.84 (m, 2H), 7.62 (m, 1H), 7.33 (m, 2H), 7.20 (m, 1H), 7.14 (t, 1H), 6.81 (m, 1H), 6.70 (m, 2H), 5.29 (s, 2H), 5.25 (s, 2H), 3.80 (s, 2H), 2.52 (s, 3H). MS (ESI) 430 (M+H)+.

Workup

  1. dissolutiondissolve)
  2. washwashed with water and brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe residue is purified by flash chromatography (10% methanol in dichloromethane)
  6. filtrationfiltered through celite
  7. concentrationThe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-cebfbb389a2446498303c224f86b6a77
Source dataset
uspto-grants-2006_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07005440B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes