3-Bromopropionaldehyde dimethylacetal → HCID 18329867, compound

HRID 2271046Notes

Reaction equation

[C:1]([C:3]1[CH:15]=[CH:14][C:6]([CH2:7][N:8]2[CH:12]=[CH:11][N:10]=[C:9]2[CH3:13])=[CH:5][C:4]=1[S:16][C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=1[Cl:24])#[N:2].C[Si](C)(C)[N-][Si](C)(C)C.[Li+].[CH3:35][O:36][CH:37]([O:41][CH3:42])[CH2:38][CH2:39]Br.C([O-])(O)=O.[Na+]>O1CCCC1.CCOC(C)=O>[C:1]([C:3]1[CH:15]=[CH:14][C:6]([CH:7]([N:8]2[CH:12]=[CH:11][N:10]=[C:9]2[CH3:13])[CH2:39][CH2:38][CH:37]([O:41][CH3:42])[O:36][CH3:35])=[CH:5][C:4]=1[S:16][C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=1[Cl:24])#[N:2]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of the product from Step D (317 mg, 0.850 mmol) in 2.0 mL of tetrahydrofuran at −78° C. was added lithium hexamethyldisilazide solution dropwise (1.02 mL, 1.02 mmol, 1.0 M in THF). After 45 minutes, 3-bromopropionaldehyde dimethyl acetal was added (0.231 mL, 1.70 mmol). The reaction was warmed to 0° C. and stirred for 2 hours, then poured into EtOAc/sat. NaHCO3 solution. The organic layer was washed with brine, dried (Na2SO4), filtered, and concentrated in vacuo. The crude product was purified by silica gel column chromatography (3-5% MeOH/CH2Cl2) to provide the desired product as a 1:1.5 mixture with the starting material.

Workup

washThe organic layer was washed with brine
dry with materialdried (Na2SO4)
filtrationfiltered
concentrationconcentrated in vacuo
customThe crude product was purified by silica gel column chromatography (3-5% MeOH/CH2Cl2)

Sources & evidence

ORD record: ord-3ca9a58e8b53478596cd4539291da5c0
Source dataset: uspto-grants-2001_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06333335B1

Reaction notes

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