Benzyl Alcohol → HCID 2145438, compound

HRID 522372Notes

Reaction equation

HRID 522372 reaction equation
C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C.[CH2:34]([OH:41])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.[Br:42][C:43]1[C:44](=[O:54])[NH:45][C:46]2[C:51]([C:52]=1O)=[CH:50][CH:49]=[CH:48][CH:47]=2>C1COCC1>[CH2:34]([O:41][C:52]1[C:51]2[C:46](=[CH:47][CH:48]=[CH:49][CH:50]=2)[NH:45][C:44](=[O:54])[C:43]=1[Br:42])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 54679311HCID 54679311, compound

Product 1

HCID 2145438HCID 2145438, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a 0° C. solution of PPh3 (1.64 g) in THF (42 mL) was added diisopropylazodicarboxylate (1.21 mL) dropwise. The mixture was stirred at 0° C. for 15 minutes before the addition of benzyl alcohol (0.52 mL) followed by quinoline alcohol from Step 1 (1.0 g). The mixture was stirred 15 minutes at 0° C. then 5 hours at room temperature. A suspension had formed at that point. The solid was filtered and washed with cold isopropanol to afford the desired product (0.78 g). LRMS (ES+) m/z 352.1 (M+Na)+.

Workup

  1. custom5 hours
  2. customat room temperature
  3. customA suspension had formed at that point
  4. filtrationThe solid was filtered
  5. washwashed with cold isopropanol

Sources & evidence

ORD record
ord-166622138bc84f3b9f4f3daa6cecfe38
Source dataset
uspto-grants-2016_05
Patent number
US09328138B2

Reaction notes

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