1-Butanol → HCID 22277869, compound

HRID 1063877Notes

Reaction equation

HRID 1063877 reaction equation
[CH2:1]([O:8][N:9]([CH2:12][C:13]1[CH:18]=[C:17]([Cl:19])[C:16]([OH:20])=[C:15]([Cl:21])[CH:14]=1)[CH:10]=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:22](O)[CH2:23][CH2:24][CH3:25].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCOC(/N=N/C(OCC)=O)=O>C(Cl)Cl>[CH2:1]([O:8][N:9]([CH2:12][C:13]1[CH:14]=[C:15]([Cl:21])[C:16]([O:20][CH2:22][CH2:23][CH2:24][CH3:25])=[C:17]([Cl:19])[CH:18]=1)[CH:10]=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 2631-ButanolHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 22277855HCID 22277855, compound

Product 1

HCID 22277869HCID 22277869, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of N-benzyloxy-N-(3,5-dichloro-4-hydroxybenzyl)formamide in methylene chloride (5 ml) was added n-butanol (110 ul, 1.2 mmol) and Polymer-bound triphenyl phosphine resin (500 mg, 1,2 mmol/g, 0.6 mmol). The reaction mixture was stirred for 0.5 h at room temperature then cooled to 0° C. A solution of DEAD (0.6 mmol, 95 ul) in methylene chloride (1 ml) was added and the reaction mixture stirred at room temperature for 16 h. The resin was filtered and washed with methylene chloride three times and the filtrate was evaporated to afford the crude N-benzyloxy-N-(4-butoxy-3,5-dichlorobenzyl)formamide as a white solid. 1H NMR (400 MHz, CDCl3) δ 8.25 (s, 1H), 7.38 (m, 3H), 7.28 (m, 2H), 7.19 (s, 2H), 4.78 (s, 2H), 4.57 (s, 2H), 4.00 (t, j=6.4 Hz, 2H), 1.82 (quint, j=7.6 Hz, 2H), 1.55(sext, j=7.6 Hz, 2H), 0.98 (t, j=7.6 Hz, 3H). M+1=382

Workup

  1. temperaturethen cooled to 0° C
  2. stirringthe reaction mixture stirred at room temperature for 16 h
  3. filtrationThe resin was filtered
  4. washwashed with methylene chloride three times
  5. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-48400bfa55214eaeb2c3eed1bb45de83
Source dataset
uspto-grants-2005_11
Patent number
US06967220B2

Reaction notes

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