Solketal → Methyl 2'-cyano-5-((2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)-4'-methylbiphenyl-3-carboxylate

HRID 1845319Notes

Reaction equation

HRID 1845319 reaction equation
[C:1]([C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[CH:5][C:4]=1[C:10]1[CH:15]=[C:14]([OH:16])[CH:13]=[C:12]([C:17]([O:19][CH3:20])=[O:18])[CH:11]=1)#[N:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:40][C:41]1([CH3:48])[O:45][CH:44]([CH2:46]O)[CH2:43][O:42]1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C(Cl)Cl>[C:1]([C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[CH:5][C:4]=1[C:10]1[CH:15]=[C:14]([O:16][CH2:46][CH:44]2[CH2:43][O:42][C:41]([CH3:48])([CH3:40])[O:45]2)[CH:13]=[C:12]([C:17]([O:19][CH3:20])=[O:18])[CH:11]=1)#[N:2]

Participants

6

Reactant 4

HCID 7528SolketalHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 58187996Methyl 2'-cyano-5-hydroxy-4'-methylbiphenyl-3-carboxylate

Product 1

HCID 58188193Methyl 2'-cyano-5-((2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)-4'-methylbiphenyl-3-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of methyl 2′-cyano-5-hydroxy-4′-methylbiphenyl-3-carboxylate (150 mg, 0.56 mmol), triphenylphosphine (220 mg, 0.84 mmol), 2,2-dimethyl-1,3-dioxolane-4-methanol (82 mg, 0.62 mmol) in CH2Cl2 (5 mL) at room temperature was slowly added a solution of diisopropyl azodicarboxylate (340 mg, 1.7 mmol) in CH2Cl2 (3 mL). The reaction mixture was stirred at room temperature overnight, and then concentrated in vacuo. The residue was purified by flash chromatography to afford the title compound.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-3eb801e7555843138b191f60bf176fb6
Source dataset
uspto-grants-2015_02
Patent number
US08946439B2

Reaction notes

Loading…