1,2-Dichloroethane → HCID 53780410, compound

HRID 1017550Notes

Reaction equation

[C:1]([S:4][CH:5]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:6][C:7]([OH:9])=[O:8])(=[O:3])[CH3:2].C(Cl)CCl.[CH2:21](O)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH2:21]([O:8][C:7](=[O:9])[CH2:6][CH:5]([S:4][C:1](=[O:3])[CH3:2])[CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

Conditions

Temperature: 0 °C

Procedure

The product from Step B (5.4 g, 26.2 mmol) was taken up in DCM (50 mL) with stirring and cooled to 0° C. EDC (6.0 g, 31.4 mmol) and DMAP (164 mg, 1.31 mmol) were added followed by benzyl alcohol (2.4 mL, 23.6 mmol). The resulting solution was stirred at room temperature overnight with the exclusion of moisture. The reaction was diluted with DCM and washed successively with 1 M HCl, water, 5% Na2CO3 solution, brine and dried, filtered and evaporated to give a dark oil. This was purified by silica gel column chromatography eluting with hexane/ethyl acetate 1:1 to give the product as an orange oil (5.98 g, 70%). 1H-NMR δ (CDCl3) 7.38-7.17 (10H, m); 5.11 (2H, s), 4.08 (1H, m), 2.96 (2H, d, J=6.4 Hz), 2.64 (2H, d, J=6.4 Hz) and 2.27 (3H, s).

Workup

stirringThe resulting solution was stirred at room temperature overnight with the exclusion of moisture
washwashed successively with 1 M HCl, water, 5% Na2CO3 solution, brine
customdried
filtrationfiltered
customevaporated
customto give a dark oil
customThis was purified by silica gel column chromatography
washeluting with hexane/ethyl acetate 1:1

Sources & evidence

ORD record: ord-54e0dfff6d79403cb7d556d4c8efbf07
Source dataset: uspto-grants-2002_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06479502B1

Reaction notes

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