Diisobutylaluminum hydride → (1-(4-Bromobenzyl)-5-methoxy-2-methyl-1H-indol-3-yl) acetaldehyde

HRID 1683987Notes

Reaction equation

[Br:1][C:2]1[CH:25]=[CH:24][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([O:16][CH3:17])=[CH:13][CH:14]=3)[C:9]([CH2:18][C:19](OC)=[O:20])=[C:8]2[CH3:23])=[CH:4][CH:3]=1.CC(C[AlH]CC(C)C)C.CCOCC.CCCCCC>C(Cl)Cl>[Br:1][C:2]1[CH:25]=[CH:24][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([O:16][CH3:17])=[CH:13][CH:14]=3)[C:9]([CH2:18][CH:19]=[O:20])=[C:8]2[CH3:23])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of ester from Step 2 (16.0 g, 39.8 mmol) in CH2Cl2 (320 mL) at -100° C. was added slowly a solution of DIBAH (1.5M/toluene, 32 mL, 47.7 mmol). The reaction was then stirred for 1-- h at -78° C., before being quenched by the addition of MeOH (3 mL), followed by 25% w/v tartaric acid (100 mL). After stirring overnight at r.t., the product was extracted with CH2Cl2. The organic layer was dried (MgSO4), filtered, and evaporated to give a pale green syrup. This was stirred vigorously with 1:4 Et2O/hexane to give 13 g of the title compound as an off-white solid.

Workup

custombefore being quenched by the addition of MeOH (3 mL)
stirringAfter stirring overnight at r.t.
extractionthe product was extracted with CH2Cl2
dry with materialThe organic layer was dried (MgSO4)
filtrationfiltered
customevaporated
customto give a pale green syrup

Sources & evidence

ORD record: ord-813fa14c004c465eae083cb4da30d8bd
Source dataset: uspto-grants-1997_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05639780

Reaction notes

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