Isopropanol → HCID 131722536, compound

HRID 1976325Notes

Reaction equation

HRID 1976325 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5](O)=[C:4]([C:9]([C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=2)=[CH2:10])[CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH:37]([OH:40])([CH3:39])[CH3:38].CCOC(/N=N/C(OCC)=O)=O>O1CCCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:38][C:37](=[O:40])[CH3:39])=[C:4]([C:9]([C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=2)=[CH2:10])[CH:3]=1

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 21996973HCID 21996973, compound2×

Product 1

HCID 131722536HCID 131722536, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a cold solution (0° C.) of 125 mg (0.4 mmol) of 4-bromo-2-[(1-p-tolyl)vinyl]phenol (Compound R) in 5 mL of tetrahydrofuran was added 125 mg (0.5 mmol) of triphenylphosphine and 0.04 mL (31 mg, 0.5 mmol) of isopropanol followed by 0.07 mL (82 mg, 0.5 mmol) of diethylazodicarboxylate. The dark yellow solution was removed from the ice bath, allowed to warm to ambient temperature on its own and stirred overnight (22.5 hours). The reaction mixture was concentrated in vacuo to a gummy yellow solid. Purification by flash chromatography (silica, 1% ethyl acetate in hexane) gave the title compound as a yellow oil.

Workup

  1. customThe dark yellow solution was removed from the ice bath
  2. concentrationThe reaction mixture was concentrated in vacuo to a gummy yellow solid
  3. customPurification by flash chromatography (silica, 1% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-5e562fccde984deb9816947ec51bce1e
Source dataset
uspto-grants-2001_05
Patent number
US06225494B1

Reaction notes

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