N,N,N',N'-Tetramethylethylenediamine → 4-(hydroxymethyl)-3,4-dihydro-2H-chromene-8-carbonitrile

HRID 2173256Notes

Reaction equation

Br[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[O:10][CH2:9][CH2:8][CH:7]2[CH2:12][OH:13].[CH3:14][N:15](CCN(C)C)C.CCOC(C)=O>CN(C=O)C.[C-]#N.[C-]#N.[Zn+2].C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[OH:13][CH2:12][CH:7]1[C:6]2[C:11](=[C:2]([C:14]#[N:15])[CH:3]=[CH:4][CH:5]=2)[O:10][CH2:9][CH2:8]1

Participants

Conditions

Temperature: 100 °C

Procedure

A solution of (8-bromo-3,4-dihydro-2H-chromen-4-yl)methanol (1 g, 4.12 mmol) in 3 mL of DMF was added Zn(CN)2 (481 mg, 4.12 mmol), Pd2(dba)3 (67 mg, 0.04 mmol), TMEDA (191 mg, 1.6 mmol), Xantphose (48 mg, 0.08 mmol), and the mixture was stirred under microwave irradiation for 5 min at 100° C. The mixture was added with 10 mL of EtOAc, washed with brine, dried over anhydrous Na2SO4 and concentrated. The residue was purified by prep-TLC to give 4-(hydroxymethyl)-3,4-dihydro-2H-chromene-8-carbonitrile.

Workup

washwashed with brine
dry with materialdried over anhydrous Na2SO4
concentrationconcentrated
customThe residue was purified by prep-TLC

Sources & evidence

ORD record: ord-74a2ab077706474a9f188b275b8fb0f3
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09056859B2

Reaction notes

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