Sodium Cyanide → HCID 59796272, compound

HRID 1093933Notes

Reaction equation

[C:1]([O:20][CH2:21][CH:22]1[CH2:26][CH:25]([CH2:27]OS(C2C=CC(C)=CC=2)(=O)=O)[CH:24]=[CH:23]1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C-:39]#[N:40].[Na+]>CN(C)C=O>[C:1]([O:20][CH2:21][CH:22]1[CH2:26][CH:25]([CH2:27][C:39]#[N:40])[CH:24]=[CH:23]1)([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To a stirred solution of compound from Step 2, toluene-4-sulfonic acid 4-trityloxymethyl-cyclopent-2-enylmethyl ester (21.3 g, 40.59 mmol) in dimethylformamide (150 mL) was added sodium cyanide (3.58 g, 73.18 mmol) at room temperature and the reaction was stirred at 70° C. for 48 h. After cooling, the reaction mixture was extracted with ethyl acetate (2×250 mL), washed with water (2×100 mL), brine (50 mL) and dried (MgSO4). After filtration, the filtrate was concentrated and the residue was purified on a silica gel column using ethyl acetate in hexanes (0 to 30%), which afforded 14.96 g (97.1%) of desired product, (4-trityloxymethyl-cyclopent-2-enyl)-acetonitrile, as a colorless solid.

Workup

temperatureAfter cooling
extractionthe reaction mixture was extracted with ethyl acetate (2×250 mL)
washwashed with water (2×100 mL), brine (50 mL)
dry with materialdried (MgSO4)
filtrationAfter filtration
concentrationthe filtrate was concentrated
customthe residue was purified on a silica gel column

Sources & evidence

ORD record: ord-8a05682d9cf74a45a14edc8d863e739a
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08133870B2

Reaction notes

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