Triphenylphosphine → HCID 21907520, compound

HRID 1247459Notes

Reaction equation

HRID 1247459 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:8]([OH:11])=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:12].[Cl:13][CH2:14][CH2:15][CH2:16]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>ClCCl>[Br:1][C:2]1[CH:10]=[CH:9][C:8]([O:11][CH2:16][CH2:15][CH2:14][Cl:13])=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:12]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 123133-Chloro-1-propanolHCID 5462977Diethyl azodicarboxylateHCID 21907553HCID 21907553, compound

Product 1

HCID 21907520HCID 21907520, compoundYield 67.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A suspension of Example 106D (250 mg, 1.1 mmol), 3-chloropropanol (0.095 mL, 1.1 mmol), and triphenylphosphine (350 mg, 1.3 mmol) in dichloromethane (5 mL) at 0° C., was treated dropwise with DEAD (0.21 mL, 1.3 mmol) over 10 minutes. The resulting mixture was stirred at 0° C. for 1 hour, warmed to room temperature overnight, and concentrated. The residue was purified by silica gel chromatography with 50 to 60% ethyl acetate/hexanes to give 227 mg of the desired product which was contaminated with triphenylphosphine oxide. MS (ESI(+)) m/e 304,306 (M+H)+.

Workup

  1. temperaturewarmed to room temperature overnight
  2. concentrationconcentrated
  3. customThe residue was purified by silica gel chromatography with 50 to 60% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-aa3b05acf0814bd4a432db150abffaff
Source dataset
uspto-grants-2006_10
Patent number
US07129260B2

Reaction notes

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