Chloroform → HCID 9812986, compound

HRID 1920570Notes

Reaction equation

C(Cl)(Cl)Cl.[CH3:5][CH:6]([OH:8])[CH3:7].C[CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]>>[C:5]1([CH:6]([OH:8])[C:7]#[C:14][CH2:13][CH2:12][CH2:11][CH3:10])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

Reactant 2

HCID 6212Chloroform

HCID 21585144Isopropanol hexane

Product 1

HCID 9812986HCID 9812986, compound

Procedure

A colorless oil. [α]D25−18.1 (c 1.3, CHCl3); 1H NMR (400 MHz, CDCl3): δ 7.54-7.52 (m, 2H), 7.38-7.28 (m, 3H), 5.43 (d, J=5.6 Hz, 1H), 2.26 (td, J=7.2, 2.0 Hz, 2H), 2.13 (d, J=5.6 Hz, 1H), 1.55-1.36 (m, 4H), 0.898 (t, J=7.2 Hz, 3H); 13C NMR (100 MHz, CDCl3): δ 141.2 (C), 128.3 (CH×2), 127.9 (CH), 126.5 (CH×2), 87.3 (C), 79.9 (C), 64.5 (CH), 30.5 (CH2), 21.8 (CH2), 18.3 (CH2), 13.4 (CH3); IR (neat) 3397, 3031, 2958, 2933, 2873, 2227, 1950, 1884, 1809, 1603, 1494, 1455, 1135, 1002, 698 cm−1; HRMS calculated for C13H16O 188.1201, found 188.1192. Chiral HPLC analysis: Chiralcel OD-H, 2-propanol/hexane (10:90), 1.0 mL/min, uv 254 nm; tR=11.0 min (87.5%), 13.8 min (12.5%), 75% ee.

Workup

customtR=11.0 min (87.5%), 13.8 min (12.5%), 75% ee

Sources & evidence

ORD record: ord-da92b89b7ac94afba702857c7ed52c8b
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08168835B2

Reaction notes

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