Dimethyl Sulfoxide → HCID 11780853, compound

HRID 322624Notes

Reaction equation

HRID 322624 reaction equation
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[CH:6]([CH2:11][CH2:12][O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:7][CH2:8][CH2:9][OH:10].C(Cl)(C(Cl)=O)=O.CS(C)=O.C(N(CC)CC)C.C(OCCC(CC=C)CO)C1C=CC=CC=1>>[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[CH:6]([CH2:11][CH2:12][O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:7][CH2:8][CH:9]=[O:10]

Participants

6

Reactant 5

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 11053183HCID 11053183, compoundHCID 22011254HCID 22011254, compound

Product 1

HCID 11780853HCID 11780853, compoundYield 81%

Procedure

The alcohol (15 (16.8 g, 59.92 mmol), prepared according to Example 13, was oxidized using 2 M (COCl)2 (37.50 mL, 75 mmol), dry DMSO (10.6 mL, 150 mmol), and triethylamine (43 mL, 300 mmol) as for the oxidation of compound 12. Similar work up as for 13 gave a crude product, which was purified by column chromatography eluting with ether/hexane (2:1), to give the aldehyde 16 (4.8 g, 81%) as a colorless oil. IR (KBr)νmax 29.42, 2878, 2725, 1723, 1496, 1434, 1413, 1368, 1211, 1153, 1098, 1031, 951, 742, 661 cm−1; 1HNMR (CDCl3)δ 1.56-1.86 (m, 5 H), 2.52 (t, J=7.6 Hz, 2H), 3.52-3.57 (m, 2H), 3.79-3.92 (m, 4 H), 4.48 (s, 2 H), 4.75 (d, J=3.3 Hz, 1 H), 7.25-7.34 (m, 5 H), 9.71 (s, 1 H); 13CNMR (CDCl3)δ 21.48, 29.33, 38.00, 41.71, 64.79, 68.73, 72.82, 106.28, 127.42, 127.55, 128.55, 128.25, 138.48; mass spectrum (EI), m/z (rel intensity) 279 (M+−1.7.5), 219(7), 171 (15), 144(8), 127(53), 91(31), 83(9), 73(100), 65(4).

Workup

  1. customSimilar work up as for 13 gave a crude product, which
  2. customwas purified by column chromatography
  3. washeluting with ether/hexane (2:1)

Sources & evidence

ORD record
ord-6dc55b256eaa4792a142061b691da03a
Source dataset
uspto-grants-2001_04
Patent number
US06211360B1

Reaction notes

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