Carbon Dioxide → trans-3-(8-Nonen-1-yl)-4-(4-pentyn-1-yl)oxetan-2-one

HRID 1044435Notes

Reaction equation

[C:1](=[O:19])(SC1C=CC=CC=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH:10]=[CH2:11].C(=O)[CH2:21][CH2:22][CH2:23][C:24]#[CH:25].[C:27](=O)=[O:28].[NH4+].[Cl-]>C1COCC1>[CH2:3]([C@H:2]1[C@H:1]([CH2:25][CH2:24][CH2:23][C:22]#[CH:21])[O:19][C:27]1=[O:28])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH:10]=[CH2:11]

Participants

Conditions

Temperature: -78 °C

Procedure

Thereafter the ice bath was replaced with an acetone-dry ice bath and the reaction mixture was cooled to −78° C. A solution of S-phenyl 10-undecenethioate 2 (55.3 mg, 0.20 mmol) in 250 THF was added dropwise via a syringe over 5 min. After stirring the mixture for 2 h at −78° C., a solution of 5-hexynal 1 (19.2 mg, 0.20 mmol) in 250 μL THF was added dropwise over 25 min via a syringe which was cooled externally by a rubber tube filled with dry ice. The reaction mixture was stirred for 30 min and then gradually warmed up to 0° C. within 75 min. Then 1 mL half-saturated NH4Cl solution was added.

Workup

temperaturewas cooled externally by a rubber tube
stirringThe reaction mixture was stirred for 30 min
temperaturegradually warmed up to 0° C. within 75 min

Sources & evidence

ORD record: ord-beaae37b5508448cad7a0f5779db7a0c
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08563598B2

Reaction notes

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