Acetyl chloride → (+)-O-Acetyl-D-malic Anhydride

HRID 2363897노트

반응식

[C:1]([OH:9])(=[O:8])[C@@H:2]([CH2:4][C:5]([OH:7])=O)[OH:3].[C:10](Cl)(=[O:12])[CH3:11]>>[C:10]([O:3][C@@H:2]1[CH2:4][C:5](=[O:7])[O:8][C:1]1=[O:9])(=[O:12])[CH3:11]

참가 물질

반응물 2

HCID 6367Acetyl chloride

HCID 92824D-Malic acid

생성물 1

HCID 9815264(+)-O-Acetyl-D-malic Anhydride

반응 조건

온도: 45 °C

실험 절차

A mixture of D-malic acid (10 g, 75 mmol, Major Chemicals Co. Ltd. lot #KS00404) in acetyl chloride (30 mL, Aldrich cat #11, 418-9) was heated to 45° C. for 6 h. The excess acetyl chloride was evaporated in vacuo and the residue was taken up in dichloromethane (10-15 mL). The volatiles were removed in vacuo and the residual oil was stored at 4° C. for 18 h. Under cold storage, the oil crystallized, giving rise to (R)-(+)-2-acetoxysuccinic anhydride (95a) as a white solid (11.7 g, quant yield); m.p. 52° C.; [α]D+23.82° (c 5.44, acetone); 1H-NMR (300 MHz, CDCl3) δ: 5.51 (dd, 1H, J 6 Hz, 9 Hz), 3.36 (dd, 1H, J 19 Hz, 9 Hz), 3.00 (dd, 1H, J 19 Hz, 6 Hz), 2.17 (s, 3H); 13C-NMR (75 MHz, CDCl3) δ: 169.61 (+), 167.66 (+), 166.21 (+), 67.51 (−), 35.10 (+), 20.16 (−).

후처리

customThe excess acetyl chloride was evaporated in vacuo
customThe volatiles were removed in vacuo
customUnder cold storage, the oil crystallized

출처 및 근거

ORD 기록: ord-97b28ee8ed7d4473b37c9f906d3cd4cd
출처 데이터셋: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US08692002B2

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