3-Hydroxybenzaldehyde → HCID 58949819, compound

HRID 1641303Notes

Reaction equation

HRID 1641303 reaction equation
CCOC(/N=N/C(OCC)=O)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:32][CH:33]([OH:36])[CH:34]=[CH2:35].O[C:38]1[CH:39]=[C:40]([CH:43]=[CH:44][CH:45]=1)[CH:41]=[O:42]>C1COCC1>[CH3:32][CH:33]([O:36][C:38]1[CH:39]=[C:40]([CH:43]=[CH:44][CH:45]=1)[CH:41]=[O:42])[CH:34]=[CH2:35]

Participants

6

Reactant 4

HCID 1013-HydroxybenzaldehydeHCID 117163-Buten-2-olHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylate

Product 1

HCID 58949819HCID 58949819, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Added DEAD (0.964 mL, 6.142 mmole) dropwise to a solution of triphenylphosphine (0.1.611 g, 6.142 mmole), 3-buten-2-ol (Fluka, 0.423 mL, 4.91 mmole), and 3-hydroxy benzaldehyde (0.5 g, 4.09 mmole) in 10 mL dry THF, at rt, under Argon. After 10 min, the reaction was concentrated in vacuo and was purified on a 35 g Redisep column eluting with a gradient of 5%-30% EtOAc in hexanes.

Workup

  1. customat rt
  2. concentrationthe reaction was concentrated in vacuo
  3. customwas purified on a 35 g Redisep column
  4. washeluting with a gradient of 5%-30% EtOAc in hexanes

Sources & evidence

ORD record
ord-9ca5f55da6ad45938aa1a2d6e9e38b95
Source dataset
uspto-grants-2012_02
Patent number
US08114887B2

Reaction notes

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