Benzyloxyacetyl chloride → HCID 12052618, compound

HRID 1936921Notes

Reaction equation

HRID 1936921 reaction equation
[C:1]1(/[CH:11]=[C:12]2/[CH:13]([OH:22])[C:14]#[C:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]#[C:21]/2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[CH2:23]([O:30][CH2:31][C:32](Cl)=[O:33])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>CN(C1C=CN=CC=1)C>[CH2:23]([O:30][CH2:31][C:32]([O:22][CH:13]1[C:14]#[C:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]#[C:21]/[C:12]/1=[CH:11]\[C:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1)=[O:33])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

4

Reactant 2

HCID 177085Benzyloxyacetyl chlorideHCID 12052610HCID 12052610, compound

Product 1

HCID 12052618HCID 12052618, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

To a solution of Compound 20b (12.1 mg, 4.37×10−2 mmol) and DMAP (57.5 mg, 0.44 mmol) in dry Ch2Cl2 (5 mL) cooled in an ice-water bath was added benzyloxyacetyl chloride (16.1 mg, 8.74×10−2 mmol) followed by stirring at room temperature for 4 hours. The reaction mixture was concentrated under reduced pressure and the residue was purified by flash column chromatography (silica gel, 20 percent EtOAc in hexane) to give 13.5 mg (73 percent) of Compound 38: pale yellow oil; Rf=0.52 (20 percent EtOAc in hexane); IR (neat) 2956, 2212, 1755, 1188, 1069 cm−1; 1H NMR (300 MHz, CDCl3) δ8.32 (d, J=7.44 Hz, 1H), 8.09-8.00 (m, 1H), 7.92-7.79 (m, 2H), 7.58-7.46 (m, 3H), 7.44-7.28 (m, 6H), 6.33 (t, J=1.35 Hz, 1H), 4.68 (s, 2H), 4.24 and 4.18 (AB q, J=16.59 Hz, 2H), 2.52-2.22 (m, 4H), 1.98-1.66 (m, 4H); 13C NMR (75 MHz, CDCl3) δ170.5, 134.2, 133.4, 132.6, 131.9, 129.8, 129.3, 129.2, 128.9, 128.7, 127.1, 127.0, 126.5, 125.9, 124.1, 123.4, 121.3, 103.4, 94.5, 80.8, 79.0, 74.1, 70.2, 68.0, 28.2, 28.1, 22.5, 21.4; MS (+CI) m/z (relative intensity) 435 (M+, 1), 271 (100).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by flash column chromatography (silica gel, 20 percent EtOAc in hexane)

Sources & evidence

ORD record
ord-874896b7f8e1483cbe53b1b6213b34b2
Source dataset
uspto-grants-2002_05
Patent number
US06391916B1

Reaction notes

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